Benzyl Alcohol → HCID 86709898, 화합물

HRID 341330노트

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HRID 341330 반응식
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH:3]=[CH:4][C:5]([OH:7])=[O:6].[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(N=C=NC2CCCCC2)CCCCC1.Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][Si:2]([CH3:9])([CH3:8])[CH:3]=[CH:4][C:5]([O:7][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6]

참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 541719853-(Trimethylsilyl)prop-2-enoic acid

생성물 1

HCID 86709898HCID 86709898, 화합물수율 94.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A solution of 3-trimethylsilylacrylic acid (510 mg, 3.54 mmol) [J. Org. Chem., 56, pp. 4766-4772, 1991] in dichloromethane (8 ml) was added successively with benzyl alcohol (0.59 ml, 5.71 mmol), dicyclohexylcarbodiimide (DCC, 914 mg, 4.44 mmol) and 4-dimethylaminopyridine (4-DMAP, 43 mg, 0.352 mmol) under ice cooling, the mixture was stirred for 5 minutes, and then stirring was further continued at room temperature for 16 hours. The reaction mixture was cooled on ice, and then added with aqueous hydrochloric acid (1 N, 5 ml), the mixture was filtered under reduced pressure, and the resulting urea was washed with ethyl acetate. After the layers were separated, the organic layer was washed with saturated aqueous sodium hydrogencarbonate and water, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel chromatography [hexane/ethyl acetate (24:1)] to obtain benzyl 3-trimethylsilylacrylate (782 mg, 94%) mentioned in the title as colorless oil.

후처리

  1. stirringstirring
  2. waitwas further continued at room temperature for 16 hours
  3. temperatureThe reaction mixture was cooled on ice
  4. filtrationthe mixture was filtered under reduced pressure
  5. washthe resulting urea was washed with ethyl acetate
  6. customAfter the layers were separated
  7. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate and water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel chromatography [hexane/ethyl acetate (24:1)]

출처 및 근거

ORD 기록
ord-3c590d4653d641acb6b2065f40f398fb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895769B2

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