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Chemical Structure| 939768-64-6

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Product Details of [ 939768-64-6 ]

CAS No. :939768-64-6
Formula : C9H16O3
M.W : 172.22
SMILES Code : O=C([C@H]1C[C@@H](O)C1)OC(C)(C)C
MDL No. :MFCD20259656
InChI Key :TYVLAZGEMLWPQS-UHFFFAOYSA-N
Pubchem ID :57478438

Safety of [ 939768-64-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501

Application In Synthesis of [ 939768-64-6 ]

* 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 [ 939768-64-6 ]

[ 939768-64-6 ] Synthesis Path-Downstream   1~2

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  • [ 939768-64-6 ]
YieldReaction ConditionsOperation in experiment
98.83% With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20℃; for 2.33333h;Inert atmosphere; A 1L three-neck bottle was charged with nitrogen, 00 condition, to the suspension of Sodium borohydride (2.389 g, 63.158 mmol) in THF (108 mL, 0.886 g/mL, 1327.029 mmol) was added the solution of 3 -oxocyclobutanecarboxylate (21.5 g, 126.316 mmol) in MeOH (52 mL, 0.791 g/mL, 1283.684 mmol) and THF (160 mL, 0.886 g/mL, 1965.969 mmol) drop by drop in 20 minutes under nitrogen atmosphere. jCaution Gasemitting reactionJ jMonitor the inner reaction system tempearture no more than20.J The reaction mixture was stirred at 00 for 2 hours, TLC (3:1 = HEX: EA) to show the consumption of all starting material. The mixture was concentrated at reduced pressure to give a residue, which was added saturated Na2CO3 solution (200 mL) and extracted with EA (300mL X 3). The combined organic layers were washed with brine,dried over Na2 S04, filtered and the filtrate was concentrated to give a crude product (21.5 g, yield 98.83%) which was used without further purification for next step. ?H NIVIR (300 1VIHz, CDC13) 4.73 -4.69 (m, 1H), 4.16 -4.14 (m, 1H), 2.64 -2.40 (m, 3H), 2.27 - 2.06 (m, 2H), 1.44 (s, 9H).
70% With sodium tetrahydroborate; ethanol; at 20 - 30℃; for 2h; Preparation No.37: 3-Hydroxy-cyclobutanecarboxylic acid teri-butyl ester; A solution of teri-butyl 3-oxocyclobutanecarboxylate (prepared according to R.P. Lemieux, J. Org. Chem. (1993), Vol. 58, No. 1, pp. 100-110) (10.5g, 61.7 mmol) in EtOH (110 mL) was treated with sodium borohydride (2.173 mL, 61.7 mmol) portion wise at RT (cold water bath used to maintain reaction temperature below about 30 C) and the reaction was stirred at room temperature for about 2 h. The reaction was diluted with saturated NaCl solution (300 mL) and extracted with EtOAc (300 mL). The EtOAc layer was washed with saturated salt solution (3 x 200 mL), dried over sodium sulfate, filtered and concentrated. The crude product was further purified by distillation, taking the fraction that boils at about 88-90C at 3 Torr to yield 3-hydroxy-cyclobutanecarboxylic acid tert-butyl ester (7.37g, 70%) as colorless oil.LC/MS (Table 1, Method a), Rt = no peak, no parent ion; .H NMR (400 MHz, DMSO-d6) delta ppm 5.12 (d, J= 6.9, 1H), 3.97-3.88 (m, 1H), 2.46-2.29 (m, 3H), 1.94-1.86 (m, 2H), 1.39 (s, 9H).
With sodium tetrahydroborate; In methanol; at -30℃; for 2.5h;Inert atmosphere; A mixture of <strong>[145549-76-4]tert-butyl 3-oxocyclobutanecarboxylate</strong> (70.0 g, 411 mmol) in MeOH (700 mL) was added NaBH4 (15.6 g, 411 mmol) at -30 C under N2 over 2 h. The reaction mixture was stirred at -30 C for 0.5 h. The reaction mixture was quenched by the addition of with ice with sat. NH4C1 (700 mL) slowly at 0 C over 30 mm. The reaction mixture was concentrated under reduced pressure to leave the aqueous phase that was extracted with EtOAc (3 x 300 mL). The combined organics were washed with brine (300 mL), dried over anhydrous Na2SO4, filtered, and concentrated. Isolated as a mixture of diastereomers in favor of the c/s-product. ?H-NMR (400 MHz, CDC13): 4.23-4.04 (m, 1H), 2.79 (br s, 1H), 2.60 -2.43 (m, 3H), 2. 14-2.05 (m, 2H), 1.43 (s, 9H).
With methanol; sodium tetrahydroborate; at -30℃; for 2.5h;Inert atmosphere; A mixture of tert-butyl 3- oxocyclobutanecarboxylate (70.0 g, 411 mmol) in MeOH (700 mL) was added NaBH4 (15.6 g, 411 mmol) at -30 °C under N2 over 2 h. The reaction mixture was stirred at -30 °C for 0.5 h. The reaction mixture was quenched by the addition of ice and aq. sat. NH4CI (700 mL) slowly at 0 °C over 30 min. The reaction mixture was concentrated under reduced pressure to leave the aqueous phase that was extracted with EtOAc (3 x 300 mL). The combined organics were washed with brine (300 mL), dried over anhydrous Na2S04, filtered, and concentrated. Mixture of diastereomers in favor of the cA-product. 'H-NMR (400 MHz, CDCI3): d 4.23-4.04 (m, 1H), 2.79 (br s, 1H), 2.60 -2.43 (m, 3H), 2.14-2.05 (m,2H), 1.43 (s, 9H).

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  • [ 1311158-43-6 ]
 

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