Ethyl bromoacetate → HCID 70410920, compound

HRID 1651377Notes

Reaction equation

HRID 1651377 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]([CH:11]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:10].Br[CH2:32][C:33](=[O:44])/[CH:34]=[CH:35]/[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=1.BrCC(OCC)=O>C1(C)C=CC=CC=1>[CH3:43][O:42][C:38]1[CH:37]=[C:36](/[CH:35]=[CH:34]/[C:33](=[O:44])/[CH:32]=[CH:11]/[C:9]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:10])[CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 23051859HCID 23051859, compoundHCID 53735909HCID 53735909, compound

Product 1

HCID 70410920HCID 70410920, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 14.9 g (35.2 mmol) of [[[2-(2-methoxyethoxy)ethoxy]carbonyl]methylene]triphenylphosphorane (preparation see paragraph (c)) in 100 ml of toluene was treated with 4.48 g (17.6 mmol) of (E)-1-bromo-4-(3-methoxyphenyl)-3-buten-2-one (preparation see paragraph d)). The reaction mixture was stirred at reflux for 2 hours and then filtered. After the addition of 1.63 ml (17.6 mmol) of ethyl bromoacetate, the filtrate was again stirred at reflux for 2 hours. The separated solid was filtered off. The filtrate was concentrated and purified by flash chromatography on 500 g of silica gel (elution agent ether/hexane 10:1). Crystallization of the purified product from methylene chloride/ether/hexane yielded 2-(2-methoxyethoxy)ethyl (E,E)-6-(3-methoxyphenyl)-4-oxo-2,5-hexadienoate of melting point 59°-60°.

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationfiltered
  3. stirringthe filtrate was again stirred
  4. temperatureat reflux for 2 hours
  5. filtrationThe separated solid was filtered off
  6. concentrationThe filtrate was concentrated
  7. custompurified by flash chromatography on 500 g of silica gel (elution agent ether/hexane 10:1)
  8. customCrystallization of the purified product from methylene chloride/ether/hexane

Sources & evidence

ORD record
ord-a77383a0d2c2403990c20d07b2d67d0f
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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