Potassium Hydroxide → HCID 67823835, compound

HRID 1492083Notes

Reaction equation

HRID 1492083 reaction equation
C[C:2]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([Br:6])([Br:5])[CH:3]1[CH3:7].[OH-].[K+].[K].[CH3:16]C1(Br)C(C(O)=O)C1(C)Br.BrC[C:28]1[CH:33]=[CH:32][CH:31]=C[C:29]=1[C:34](=[CH:39][O:40][CH3:41])[C:35]([O:37][CH3:38])=[O:36]>C(O)C.CN1CCCC1=O>[CH3:16][CH:11]([O:10][C:8]([CH:2]1[C:4]([Br:5])([Br:6])[CH:3]1[CH3:7])=[O:9])[C:12]1[CH:31]=[CH:32][CH:33]=[CH:28][C:29]=1[C:34](=[CH:39][O:40][CH3:41])[C:35]([O:37][CH3:38])=[O:36]

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 12406051Ethyl 2,2-dibromo-1,3-dimethylcyclopropane-1-carboxylate2×HCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoateHCID 131718792HCID 131718792, compound

Product 1

HCID 67823835HCID 67823835, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 11.0 g (36 mmol) of ethyl 1,2-dimethyl-3,3-dibromocyclopropanecarboxylate (prepared according to Intermediate 12a) and 2.2 g (40 mmol) of potassium hydroxide in 100 ml of ethanol was stirred for 6 hours at 60° C. 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 dimethyldibromocyclopropanecarboxylic acid in 60 ml of N-methylpyrrolidone with 5.1 g (18 mmol) of methyl alpha- (2-bromomethylphenyl ) -beta-methoxyacrylate was carried out similarly to Example 1. After hydrolysis of the reaction mixture, the product was extracted with methyl tert-butyl ether and was isolated and purified similarly to Example 1. Yield: 32% colorless oil.

Workup

  1. customevaporated down
  2. customafter which the resulting precipitate was separated off
  3. washwashed with diethyl ether
  4. customAfter hydrolysis of the reaction mixture
  5. extractionthe product was extracted with methyl tert-butyl ether
  6. customwas isolated
  7. custompurified similarly to Example 1

Sources & evidence

ORD record
ord-bf5545f52c904817a2b8dda34759200b
Source dataset
uspto-grants-1994_12
Patent number
US05371268

Reaction notes

Loading…