Benzyl bromoacetate → Benzyl 2-hydroxyacetate

HRID 241547

반응식

HRID 241547 반응식
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C1(C)C=CC=CC=1.C([O:22]CC)C>C(Cl)(Cl)Cl.C(#N)C.C(=O)([O-])[O-].[Ag+2]>[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH2:2][OH:22]

참가 물질

6

반응물 2

HCID 62576Benzyl bromoacetateHCID 22238780Ether toluene

생성물 1

HCID 561337Benzyl 2-hydroxyacetate수율 46%

시약·촉매·용매 3

HCID 178418647HCID 178418647, 화합물촉매HCID 6212Chloroform용매HCID 6342Acetonitrile용매

실험 절차

To a mixture of pentanoracid 7 (600 mg; 1.2 mmol), silver carbonate (440 mg; 1.6 mmol) in a mixture of chloroform (10 ml) and acetonitrile (7 ml), benzyl bromacetate (260 μl; 1.6 mmol) was added and the reaction mixture was stirred for 28 hours at room temperature. The course of the reaction was monitored by TLC (toluene/diethyl ether 6:1). The reaction mixture was then filtered through diatomaceous earth and the filtrate was worked-up and the product was purified by analogical procedure as in the preparation of 21-oxoacid benzyl glycolate. The obtained crude pentanoracid benzyl glycolate (358 mg; 46%) having m.p. 156-157° C. (methanol), [α]D=+57° (c=0.31) was used in the next step.

후처리

  1. additionwas added
  2. filtrationThe reaction mixture was then filtered through diatomaceous earth
  3. customthe product was purified by analogical procedure as in the preparation of 21-oxoacid benzyl glycolate

출처 및 근거

ORD 기록
ord-ad35902827f84728ac84b2bd8c661cb4
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653056B2

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