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Chemical Structure| 1111-97-3 Chemical Structure| 1111-97-3

Structure of 1111-97-3

Chemical Structure| 1111-97-3

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Product Details of [ 1111-97-3 ]

CAS No. :1111-97-3
Formula : C5H7Cl
M.W : 102.56
SMILES Code : C#CC(C)(Cl)C
MDL No. :MFCD00190221
InChI Key :QSILYWCNPOLKPN-UHFFFAOYSA-N
Pubchem ID :70679

Safety of [ 1111-97-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H302+H312+H332
Precautionary Statements:P210-P261-P280-P304+P340-P312
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 1111-97-3 ]

* 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 [ 1111-97-3 ]

[ 1111-97-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1111-97-3 ]
  • [ 6174-86-3 ]
  • 3-chloro-7-(1,1-dimethyl-prop-2-ynyloxy)-4-methyl-chromen-2-one [ No CAS ]
  • 2
  • [ 1111-97-3 ]
  • [ 111669-25-1 ]
  • [ 12775-96-1 ]
  • [ 147539-49-9 ]
YieldReaction ConditionsOperation in experiment
copper(I) chloride; In N-methyl-acetamide; PREPARATION 65 1-[1,1-Dimethylethoxycarbonyl]-4-[3-(1,1-dimethylprop-2-ynylamino)-2-pyridinyl]piperazine To a mixture of <strong>[111669-25-1]1-[1,1-dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine</strong> (International Publication No. WO 88/08424, 5.40 g), cuprous chloride (1.00 g), copper powder (1.00 g), and dry dimethylformamide (25 ml) under nitrogen at 0 is added a solution of 3-chloro-3-methyl-1-butyne (2.00 g) in dry dimethylformamide (5 ml) in 4 portions over 15 min. The resulting mixture is then stirred at 20-25 for 16 hrs, concentrated, and diluted with methylene chloride (75 ml) and water (20 ml). The layers are separated and the aqueous phase is extracted with methylene chloride (25 ml). The combined organic phase is washed with saline (20 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue which is chromatographed on silica gel (70-230 mesh, 500 g), eluding with a gradient of ethyl acetate/hexane (10/90-20/80). Pooling of fractions giving an Rf =0.31 (ethyl acetate/hexane, 25/75) and removal of solvent under reduced pressure gives the title compound, NMR (CDCl3) 7.75, 7.47, 6.94, 4.61, 3.56, 3.00, 2.39, 1.64 and 1.48 delta.
  • 3
  • [ 1111-97-3 ]
  • [ 99-93-4 ]
  • ethereal hydrogen chloride [ No CAS ]
  • [ 19013-07-1 ]
YieldReaction ConditionsOperation in experiment
With N-benzyl-trimethylammonium hydroxide; In methanol; dichloromethane; water; N,N-diethylaniline; (b) 6-Acetyl-3,4-dihydro-2,2-dimethyl-trans-4-isopropylamino-2H-benzo[b]pyran-3-ol hydrochlorides p-Hydroxyacetophenone (33.66 g), sodium hydroxide pellets (14.80 g), 40% benzyltrimethylammonium hydroxide in methanol (51.75 g) and 3-methyl-3-chlorobutyne (61.25 g) were stirred in water (225 ml) and dichloromethane (225 ml) for 4 days at room temperature. After separation of the layers, the aqueous layer was extracted twice with chloroform, and the combined organic phase evaporated leaving a viscous liquid which was taken up in ether and washed three times with 10% sodium hydroxide solution and once with water before drying over sodium sulphate. Removal of drying agent and solvent, and distillation at 1.0 mm Hg gave an oil (55.31 g) which was dissolved in N,N-diethylaniline (275 ml) and heated at 210-220 C. for 8 hours under nitrogen. The major part of the solvent was distilled off, and treatment of an ethereal solution of the residue with anhydrous ethereal hydrogen chloride precipitated the remainder, leaving an oil after solvent evaporation which was distilled giving 6-acetyl-2,2-dimethyl-2H-benzo[b]pyran (40.02 g), b.p. 100-102/0.2 mm Hg.
  • 4
  • [ 1111-97-3 ]
  • [ 38183-03-8 ]
  • [ 6674-22-2 ]
  • [ 786706-00-1 ]
YieldReaction ConditionsOperation in experiment
69% With CuCl2; In acetonitrile; Example 29 7,8-Bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-chromen-4-one To a suspension of 7,8-dihydroxy-2-phenyl-chromen-4-one (510 mg, 2 mmol) and CuCl2 (16 mg, 0.12 mmol) in acetonitrile (3 mL) was added 3-chloro-3-methyl-1-butyne (0.5 mL, 4.56 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.78 mL, 5.2 mmol) slowly at 0 C. The dark mixture was stirred at 0 C. for 5 h and then at room temperature overnight. The solvent was evaporated and the residue was purified by column chromatography (SiO2, EtOAc:hexanes/10-50%) to give the title compound as a white solid (540 mg, 69%): 1H NMR (CDCl3, 300 MHz) delta 8.02 (m, 2H), 7.96 (d, J=9.0 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.53 (m, 3H), 6.78 (s, 1H), 2.66 (s, 1H), 2.26 (s, 1H), 1.81 (s, 6H), 1.76 (s, 6H).
  • 5
  • [ 1111-97-3 ]
  • [ 38183-03-8 ]
  • [ 786706-00-1 ]
YieldReaction ConditionsOperation in experiment
62% With copper(l) iodide; potassium carbonate; potassium iodide; In acetone; at 50℃; for 4h; General procedure: To a solution of 11a (500.0 mg, 2.1 mmol) or 11b (555.0 mg, 2.1 mmol) in acetone (20.0 mL), potassium iodide (1.7 g, 10.5 mmol), potassium carbonate (1.5 g, 10.5 mmol) and CuI (114.6 mg, 0.6 mmol) were added. The reaction mixture was stirred at room temperature for 10 min, then 2-chloro-2-methylbut-3-yne (1.72 g, 16.8 mmol) was added and the resulted mixture was stirred at 50 C for 4 h. Water (30.0 mL) and EtOAc (30.0 mL) were added to the mixture and stirred for 30 min. The organic layer was separated, dried over sodium sulfate, and evaporated. The residue was purified through column chromatography (eluent, PE/EtOAc = 8:1) to afford 12a or 12b.
  • 6
  • [ 1111-97-3 ]
  • [ 137215-27-1 ]
  • [ 1337971-59-1 ]
 

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