Ethanol → HCID 67823526, compound

HRID 1492082Notes

Reaction equation

HRID 1492082 reaction equation
C[C:2]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4][CH:3]1[CH3:5].[OH-].[K+].BrC[C:15]1[CH:20]=[CH:19][CH:18]=C[C:16]=1[C:21](=[CH:26][O:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23].[CH2:29](O)C>>[CH3:29][CH:9]([O:8][C:6]([CH:2]1[CH2:4][CH:3]1[CH3:5])=[O:7])[C:10]1[CH:18]=[CH:19][CH:20]=[CH:15][C:16]=1[C:21](=[CH:26][O:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 14996291HCID 14996291, compoundHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

Product 1

HCID 67823526HCID 67823526, compoundYield 69%

Procedure

A stirred solution of 3.8 g (27 mmol) of ethyl 1,2-dimethylcyclopropanecarboxylate and 1.6 g (29 mmol) of potassium hydroxide in 50 ml of ethanol was refluxed for 8 hours and then evaporated down. The solution was covered with a layer of diethyl ether, after which the resulting precipitate was separated off and washed with diethyl ether. Subsequent reaction of the resulting potassium salt of dimethylcyclopropanecarboxylic acid in 60 ml of N-methylpyrrolidone, at 100° C., with 4.2 g (15 mmol) of methyl alpha-(2-bromomethylphenyl)-beta-methoxyacrylate and purification of the end product were carried out similarly to Example 1. Yield: 69%; colorless oil.

Workup

  1. customevaporated down
  2. customafter which the resulting precipitate was separated off
  3. washwashed with diethyl ether
  4. customSubsequent reaction of the resulting potassium salt of dimethylcyclopropanecarboxylic acid in 60 ml of N-methylpyrrolidone

Sources & evidence

ORD record
ord-ea3fc293a59e48748b39bbc8666e81d5
Source dataset
uspto-grants-1994_12
Patent number
US05371268

Reaction notes

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