Benzyl bromoacetate → Benzyl 2-hydroxyacetate

HRID 241547

Reaction equation

HRID 241547 reaction equation
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]

Participants

6

Reactant 2

HCID 62576Benzyl bromoacetateHCID 22238780Ether toluene

Product 1

HCID 561337Benzyl 2-hydroxyacetateYield 46%

Reagents, catalysts & solvents 3

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ad35902827f84728ac84b2bd8c661cb4
Source dataset
uspto-grants-2014_02
Patent number
US08653056B2

Linked notes

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