Ethyl Acetate → Ethyl 4-(m-methoxyphenyl)-3-phenyl-3-hydroxybutyrate

HRID 2085055

반응식

HRID 2085055 반응식
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]([O:14][CH2:15][CH3:16])(=[O:13])[CH3:12].[C:17]1([C:23]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=2)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH2:25][C:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:24])[CH2:12][C:11]([O:14][CH2:15][CH3:16])=[O:13])[CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 27596142-(3-Methoxyphenyl)-1-phenylethan-1-oneHCID 57426343Lithium bis(trimethylsilyl)amide

생성물 1

HCID 22602685Ethyl 4-(m-methoxyphenyl)-3-phenyl-3-hydroxybutyrate수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

Lithium hexamethyidisilazane (88.5 mL, 88.5 mmol) was added to THF (150 mL) at −78° C. After 15 minutes, ethyl acetate (7.79 g, 88.5 mmol) was added over 10 minutes and stirred at −78° C. for 30 minutes. The m-methoxybenzyl phenyl ketone in (10.0 g, 44.25 mmol) THF (100 mL) was added over 15 minutes and kept at that temperature for 3 hours. The reaction mixture was quenched at that temperature with saturated ammonium chloride (15 mL). The reaction mixture was diluted with ether (200 mL) and the organic layer was washed with brine, (100 mL), dried and concentrated to afford the desired product (12 g, 86% yield). NMR was consistent with the desired structure.

후처리

  1. waitkept at that temperature for 3 hours
  2. customThe reaction mixture was quenched at that temperature with saturated ammonium chloride (15 mL)
  3. additionThe reaction mixture was diluted with ether (200 mL)
  4. washthe organic layer was washed with brine, (100 mL)
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0d7cb346805c40b583610cf6d62715e4
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06720315B2

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