Benzyl Bromide → 4-Hydroxy-2,2-dimethyl-butyric acid benzyl ester

HRID 1289872

반응식

HRID 1289872 반응식
[K+].[OH:2][CH2:3][CH2:4][C:5]([CH3:10])([CH3:9])[C:6]([O-:8])=[O:7].[C:11]1([CH2:17]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C=O)C>[C:11]1([CH2:17][O:7][C:6](=[O:8])[C:5]([CH3:10])([CH3:9])[CH2:4][CH2:3][OH:2])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 7498Benzyl BromideHCID 23712640Potassium 4-hydroxy-2,2-dimethylbutyrate

생성물 1

HCID 141523044-Hydroxy-2,2-dimethyl-butyric acid benzyl ester수율 72.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-hydroxy-2,2-dimethylbutyric acid monopotassium salt (10.6 g,62.35 mmol) and phenylmethyl bromide (11.63 g, 68 mmol) in 100 ml of DMF was stirred at room temperature for 24 hours and then the mixture was poured into ice/water. The mixture was extracted with ether (3×) and the organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (silica, 12-66% of ethyl acetate/hexane) to afford 10.02 g (72%) of 4-hydroxy-2,2-dimethylbutyric acid phenylmethyl ester.

후처리

  1. extractionThe mixture was extracted with ether (3×)
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica, 12-66% of ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-1c8f11f91bd54ba8b74aafa15554c51d
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750550

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