Ethyl bromoacetate → HCID 23466036, compound

HRID 2049695Notes

Reaction equation

HRID 2049695 reaction equation
[C:1]([O:4][CH:5]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:7](=[O:9])[CH3:8])(=[O:3])[CH3:2].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>[Zn]>[OH:9][C:7]([CH3:8])([CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 234660175-Oxo-1-phenylhexan-3-yl acetate

Product 1

HCID 23466036HCID 23466036, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Using 1.48 g of 4-acetoxy-6-phenylhexan-2one, 1 ml of ethyl bromoacetate and 0.62 g of zinc, the reaction and the purification of the product were carried out according to the method described in Example 1 (a) affording 1.03 g of ethyl 3-hydroxy-3-methyl-5-acetoxy-7-phenylheptanoate. The ester (0.90 g) thus obtained was dissolved in 5 ml of methanol and 2 ml of 4 N sodium hydroxide was added thereto. The mixture was stirred for 4 hours at room temperature, acidified by the addition of 4 N hydrocholoric acid, 5 ml of ethyl acetate was added and the mixture was stirred for 3 days. The usual treatment of the organic solvent layer afforded 400 mg of the desired compound.

Workup

  1. customthe reaction
  2. customthe purification of the product

Sources & evidence

ORD record
ord-e879f96c50ab4a0cbdd44eafbddbe4ad
Source dataset
uspto-grants-1980_04
Patent number
US04198425

Reaction notes

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