Water → HCID 67905085, compound

HRID 1885906Notes

Reaction equation

HRID 1885906 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(COC)OC.[Zn].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:18]1([C:17]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[O:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

Product 1

HCID 67905085HCID 67905085, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5 g (17.5 mmol) of methyl α-(2-bromomethylphenyl)-β-methoxyacrylate and 2.5 g (17.8 mmol) of benzoyl chloride in 50 ml of dimethoxyethane is added dropwise to 2.3 g (0.035 mol) of zinc powder and 600 mg (0.9 mmol) of Pd(Ph3P)2Cl2 under nitrogen and the mixture is then heated at 50° C. for 30 minutes. Water is added, the mixture is extracted with ethyl acetate and the organic phase is dried and evaporated down. The residue is chromatographed over silica gel using hexane/ethyl acetate. 1.6 g of compound No. 1 (Table 1) are obtained as a pale yellow solid of melting point 97°-99° C. Yield: 29%.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. customthe organic phase is dried
  3. customevaporated down
  4. customThe residue is chromatographed over silica gel
  5. custom1 (Table 1) are obtained as a pale yellow solid of melting point 97°-99° C

Sources & evidence

ORD record
ord-be2fb03c597d4540aa0057fab5459fa4
Source dataset
uspto-grants-1992_09
Patent number
US05147892

Reaction notes

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