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Structure of 151155-53-2

Chemical Structure| 151155-53-2

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Product Details of [ 151155-53-2 ]

CAS No. :151155-53-2
Formula : C9H10O2
M.W : 150.17
SMILES Code : OCC1=C(OCC2)C2=CC=C1
MDL No. :MFCD06411535
InChI Key :WUXXIPOWZJYRNE-UHFFFAOYSA-N
Pubchem ID :2795020

Safety of [ 151155-53-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of [ 151155-53-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 151155-53-2 ]

[ 151155-53-2 ] Synthesis Path-Downstream   1~13

YieldReaction ConditionsOperation in experiment
Borane dimethyl-sulphide complex (60 ml) was added to a stirred solution of the above acid (70.2 g) and tetrahydrofuran (500 ml). The mixture was stirred for 30 minutes, then water (200 ml) was carefully added. The tetrahydrofuran was removed in vacuo. Water (200 ml) and then aqueous sodium hydroxide solution were added. The product was extracted into ether, and the extracts dried over potassium carbonate. The solvent was removed in vacuo to yield 7-hydroxymethyl-2,3-dihydrobenzo[b]furan (50 g) as an oil.
  • 2
  • [ 151155-53-2 ]
  • [ 870061-72-6 ]
YieldReaction ConditionsOperation in experiment
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; EXAMPLE 29B 7-(bromomethyl)-2,3-dihydro-1-benzofuran Example 29A (4.06 g, 27.1 mmol) and carbon tetrabromide (10.9 g, 32.8 mmol) were combined in methylene chloride (100 mL) at 0 C. and treated with triphenylphosphine (8.53 g, 32.6 mmol) portionwise. The mixture was allowed to warm to room temperature, was stirred overnight, concentrated under reduced pressure, and the residue was purified by flash chromatography (2% ethyl acetate/hexanes) to provide the title compound. 1H NMR (CDCl3) δ 3.22 (t, 2H), 4.50 (s, 2H), 4.65 (t, 2H), 6.81 (t, 1H), 7.12 (m, 2H).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; The product of Example 48A (4.06 g) and carbon tetrabromide (10.9 g) were combined in methylene chloride (100 mL) at 0 C and treated with triphenylphosphine (8.53 g) portionwise. The mixture was allowed to warm to room temperature, stirred overnight, concentrated under reduced pressure, and the residue was purified by flash chromatography (2% ethyl acetate/hexanes) to provide the title compound. 1H NMR (CDC13) 3.22 (t, 2H), 4.50 (s, 2H), 4.65 (t, 2H), 6.81 (t, 1H), 7.12 (m, 2H).
  • 3
  • [ 35700-40-4 ]
  • [ 151155-53-2 ]
YieldReaction ConditionsOperation in experiment
100% With borane-THF; In tetrahydrofuran; at 20 - 60℃; for 3.5h; 1M Borane-THF complex THF solution (193 mL, 193.35 mmol) was slowly added to a solution of 2,3-dihydrobenzofuran-7-carboxylic acid (10.58 g, 64.45 mmol) in THF (65 mL) over 30 min while the reaction solution was maintained at room temperature. The reaction mixture was stirred at 60C for 3.5 hr, and poured into ice (about 400 g). The mixture was stirred at room temperature for 30 min, and extracted three times with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give (2,3-dihydrobenzofuran-7-yl)methanol (9.76 g, 65.0 mmol, quant.) as a colorless oil.
77% With diborane; In tetrahydrofuran; at 0 - 20℃; A. 2,3-dihydro-l-benzofuran-7-ylmethanol [00878] Added BH3 (1M in THF, 9 mL) to a solution of 2,3-dihydro-l-benzofuran-7- carboxylic acid (481 mg, 2.93 mmol) in THF (7 mL) drop wise at 0C, thereto, the mixture was stirred at room temperature overnight. Extracted with ethyl acetate twice, and washed the organic phase with brine and dried with anhydrous Na2S04, concentrated to give the title compound (340 mg, 77%). 1H NMR (400 MHz, CDC13): delta 2.09 (1H, s), 3.22 (2H, t, J= 8.8 Hz), 4.61 (2H, t, J= 8.8 Hz), 4.67 (2H, s), 6.83 (1H, t, J= 7.6 Hz), 7.08 (1H, d, J= 7.2 Hz), 7.14 (1H, d, J= 7.2 Hz).
EXAMPLE 29A 2,3-dihydro-1-benzofuran-7-ylmethanol 2,3-Dihydrobenzofuran carboxylic acid (5.047 g, 30.77 mmol) in tetrahydrofuran at -10 C. was treated dropwise with a solution of 1.0 M borane-tetrahydrofuran (20 mL 20 mmol). The temperature was allowed to warm to room temperature overnight, and was then treated with additional 1.0 M borane-tetrahydrofuran (10 mL 10 mmol), and stirred at room temperature for 2 hours. The mixture was cooled to 5 C., slowly treated with methanol (20 mL), and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate (2*), saturated sodium chloride, dried (sodium sulfate), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (hexanes:ethyl acetate, 3:2) to provide the title compound. MS (DCI/NH3) M/Z 168 (M+NH4)+; 1H NMR (CDCl3) delta 3.21 (t, 2H), 4.60 (t, 2H), 4.68 (s, 2H), 6.83 (t, 1H), 7.08 (dd, 1H), 7.14 (dd, 1H).
With borane-THF; In tetrahydrofuran; at -10 - 20℃; for 2h; 2,3-Dihydrobenzofuran carboxylic acid (5.047g) in tetrahydrofuran at -1 0 C was treated dropwise with a solution of 1.0 M borane-tetrahydrofuran (20 mL). The temperature was allowed to warm to room temperature overnight, treated with additional 1.0 M borane-tetrahydrofuran (10 mL), and stirred at room temperature for 2 hours. The mixture was cooled to 5 C, slowly treated with methanol (20 mL), and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate (2x), saturated sodium chloride, dried (sodium sulfate), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (hexanes:ethyl acetate, 3: 2) to provide the title compound. MS (DCI/NH3) m/z 168 (M+NH4)+;1H NMR (CDC13) 5 3.21 (t, 2H), 4.60 (t, 2H), 4.68 (s, 2H), 6.83 (t, 1 H), 7.08 (dd, 1 H), 7.14 (dd, 1H).
[0359] 2,3-Dihydrobenzofuran-7-carboxylic acid (820 mg, 5 mmol) was dissolved inTHF (10 rtiL). To the solution was added TEA (0.7 mL, 5 mmol) and methylchloroformate (0.43 mL, 5 mmol). The solution was stirred for 0.5 hour. The white precipitates were removed by filtration, the filtrate was added to a solution OfNaBH4 (437 mg, 12.5 mmol) in H2O (5 mL). The resulting solution was stirred overnight. The reaction mixture was neutralized with 2 M aqueous HCl solution and then extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude alcohol was dissolved in DCM. To the solution was added PCC (1.83 g, 7.5 mmol). The mixture was stirred for 2 hours at room temperature and diluted with diethyl ether, then ether layers were decanted. Combined organic layer was filtered though a layer of Celite. The filtrate was concentrated to give crude product. The crude was purified from column with 10% EtOAc/hexane to afford 450 mg of 2,3-dihydrobenzofuran-7-carbaldehyde as a slightly yellow solid. HPLC 4.3 min.

  • 4
  • [ 151155-53-2 ]
  • [ 196799-45-8 ]
YieldReaction ConditionsOperation in experiment
77% With manganese(IV) oxide; In toluene; at 60℃; for 3h; A mixture of <strong>[151155-53-2](2,3-dihydrobenzofuran-7-yl)methanol</strong> (9.76 g, 64.99 mmol) and manganese dioxide (45.2 g, 519.93 mmol) in toluene (250 mL) was stirred at 60C for 3 hr. The manganese dioxide was filtered off, and the filtrate was concentrated under reduced pressure. The precipitate was collected by filtration and washed with cooled hexane to give 2,3-dihydrobenzofuran-7-carbaldehyde (7.43 g, 50.1 mmol, 77%) as a pale yellow solid.
With pyridinium chlorochromate; In dichloromethane; at 20℃; for 2h; [00323] 2,3-Dihydrobenzofuran-7-carboxylic acid (820 mg, 5 mmol) was dissolved inTHF (10 mL). To the solution was added TEA (0.7 mL, 5 mmol) and methylchloroformate (0.43 mL, 5 mmol). The solution was stirred for 0.5 hour. The white precipitates were removed by filtration, the filtrate was added to a solution OfNaBH4 (437 mg, 12.5 mmol) in H2O (5 mL). The resulting solution was stirred overnight. The reaction mixture was neutralized with 2 M aqueous HCl solution and then extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude alcohol was dissolved in DCM. To the solution was added PCC (1.83 g, 7.5 mmol). The mixture was stirred for 2 hours at room temperature and diluted with diethyl ether, then ether layers were decanted. Combined organic layer was filtered though a layer of Celite. The filtrate was concentrated to give crude product. The crude was purified from column EPO <DP n="307"/>with 10% EtOAc/hexane to afford 450 mg of 2,3-dihydrobenzofuran-7-carbaldehyde as a slightly yellow solid. HPLC 4.3 min.
With pyridinium chlorochromate; In dichloromethane; at 20℃; for 2h; [0359] 2,3-Dihydrobenzofuran-7-carboxylic acid (820 mg, 5 mmol) was dissolved inTHF (10 rtiL). To the solution was added TEA (0.7 mL, 5 mmol) and methylchloroformate (0.43 mL, 5 mmol). The solution was stirred for 0.5 hour. The white precipitates were removed by filtration, the filtrate was added to a solution OfNaBH4 (437 mg, 12.5 mmol) in H2O (5 mL). The resulting solution was stirred overnight. The reaction mixture was neutralized with 2 M aqueous HCl solution and then extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude alcohol was dissolved in DCM. To the solution was added PCC (1.83 g, 7.5 mmol). The mixture was stirred for 2 hours at room temperature and diluted with diethyl ether, then ether layers were decanted. Combined organic layer was filtered though a layer of Celite. The filtrate was concentrated to give crude product. The crude was purified from column with 10% EtOAc/hexane to afford 450 mg of 2,3-dihydrobenzofuran-7-carbaldehyde as a slightly yellow solid. HPLC 4.3 min.
  • 5
  • C11H10O5 [ No CAS ]
  • [ 151155-53-2 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; water; In tetrahydrofuran; [00323] 2,3-Dihydrobenzofuran-7-carboxylic acid (820 mg, 5 mmol) was dissolved inTHF (10 mL). To the solution was added TEA (0.7 mL, 5 mmol) and methylchloroformate (0.43 mL, 5 mmol). The solution was stirred for 0.5 hour. The white precipitates were removed by filtration, the filtrate was added to a solution OfNaBH4 (437 mg, 12.5 mmol) in H2O (5 mL). The resulting solution was stirred overnight. The reaction mixture was neutralized with 2 M aqueous HCl solution and then extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude alcohol was dissolved in DCM. To the solution was added PCC (1.83 g, 7.5 mmol). The mixture was stirred for 2 hours at room temperature and diluted with diethyl ether, then ether layers were decanted. Combined organic layer was filtered though a layer of Celite. The filtrate was concentrated to give crude product. The crude was purified from column EPO <DP n="307"/>with 10% EtOAc/hexane to afford 450 mg of 2,3-dihydrobenzofuran-7-carbaldehyde as a slightly yellow solid. HPLC 4.3 min.
  • 6
  • [ 151155-53-2 ]
  • [ 124-63-0 ]
  • [ 1071448-66-2 ]
YieldReaction ConditionsOperation in experiment
(2,3-dihydro-benzofuran-7-yl)-methanol (1.50 g, 10.00 mmol) was dissolved in dichloromethane and cooled to -55 C., then MsCl (1.30 mL, 16.80 mmol) was added, followed by addition of Et3N (3.0 mL, 21.52 mmol). The resulting reaction mixture was stirred at this temperature for 2 hours, then saturated aq ammonium chloride was added. The reaction mixture was extracted with ether. The combined organic phases were washed with brine, then dried over magnesium sulfate and concentrated to give the crude mesylate. The mesylate was then dissolved in DMSO, and treated with NaN3 (1.30 g, 20.00 mmol) at room temperature for 14 hours. The reaction mixture was diluted with water, and extracted with ether. The combined organic phases were washed with water, brine, and then dried over magnesium sulfate and concentrated to afford the desired azide. This azido compound was then dissolved in THF:H2O (3:1), Ph3P (2.70 g, 10.29 mmol) was added, followed by KOH (600 mg, 10.69 mmol). The resulting mixture was stirred for 14 hours. The reaction mixture was then diluted with H2O and slowly acidified with HCl and the aqueous layer was washed with Et2O (3×50 mL). The aqueous layer was then basified with NaOH (pH 14) and extracted with Et2O (3×50 mL). The combined organic extracts were washed with H2O (1×25 mL), brine (1×25 mL), dried over K2CO3 and concentrated to give the desired title amine.
  • 7
  • [ 196799-45-8 ]
  • [ 151155-53-2 ]
YieldReaction ConditionsOperation in experiment
2,3-Dihydro-benzofuran-7-carbaldehyde (1.50 g, 10.20 mmol) was dissolved in ether, then cooled to 0 C., NaBH4 (400 mg, 10.57 mmol) in MeOH (5.00 mL) was added. The resulting reaction mixture was stirred for 30 min, then saturated ammonium chloride was added. The mixture was extracted with ether, and the combined organic phases were washed with brine, then dried over magnesium sulfate and concentrated to afford the desired alcohol
  • 8
  • [ 151155-53-2 ]
  • 7-chloromethyl-2,3-dihydrobenzo[b]furan [ No CAS ]
  • 10
  • [ 151155-53-2 ]
  • 1-(2,3-dihydro-1-benzofuran-7-yl)methanamine [ No CAS ]
  • 11
  • [ 151155-53-2 ]
  • ethyl 2-(5'-hydroxy-1',3'-dihydrospiro[azetidine-3,2'-inden]-1-yl)acetate [ No CAS ]
  • ethyl 2-(5’-((2,3-dihydrobenzofuran-7-yl)methoxy)-1’,3’-dihydrospiro[azetidine-3,2’-inden]-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
15 mg To a 50 mL round bottom flask containinig PS-Triphenylphosphine (a resin-bound triphenylphosphine, 183 mg, 0.344 mmol) was added a solution of ethyl 2-(5'- hydroxy-l',3'-dihydrospiro[azetidine-3,2'-inden]-l-yl)acetate (60 mg, 0.230 mmol) in THF (0.5 mL). The suspension was allowed to stand for 5 min and then a solution of di-tert-butyl azodicarboxylate (79 mg, 0.344 mmol) in THF (0.5 mL) was added. A further 0.5 mL THF was added and the solution agitated at RT for 30 min. A solution of <strong>[151155-53-2]2,3-dihydrobenzo[b]furan-7-methanol</strong> (35 mg, 0.233 mmol) in THF (0.5 niL) was added and the reaction was stirred overnight.The reaction mixture was diluted with CH2CI2 and water and stirred for 5 min at RT. After phase separation with a Chromabond PTS-cartridge the organic layer was evaporated. The residue was purified by using the Isco-Combiflash (4 g, 0-10% MeOH in CH2CI2, 18 mL/min).Yield: 15 mg yellow oil
  • 12
  • [ 496-16-2 ]
  • [ 151155-53-2 ]
  • 13
  • [ 1091606-28-8 ]
  • [ 151155-53-2 ]
 

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