4-Phenoxybutyltriphenylphosphonium bromide → Ethyl (2E)-3-{4-[5-phenoxypent-1-en-1-yl]phenyl}acrylate

HRID 1782761Notes

Reaction equation

HRID 1782761 reaction equation
[Br-].[O:2]([CH2:9][CH2:10][CH2:11][CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.[CH:37]([C:39]1[CH:51]=[CH:50][C:42]([CH:43]=[CH:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:41][CH:40]=1)=O>C1COCC1>[O:2]([CH2:9][CH2:10][CH2:11][CH:12]=[CH:37][C:39]1[CH:40]=[CH:41][C:42](/[CH:43]=[CH:44]/[C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:50][CH:51]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 497827854-Phenoxybutyltriphenylphosphonium bromideHCID 534066763-(4-Formylphenyl)-2-propenoic acid ethyl esterHCID 178418339Butyllithium

Product 1

HCID 69353623Ethyl (2E)-3-{4-[5-phenoxypent-1-en-1-yl]phenyl}acrylateYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

3.16 g of (4-phenoxybutyl)(triphenyl)phosphonium bromide are suspended in 25 ml of THF under argon and cooled to −40° C. 2.36 ml of n-butyllithium (1.6 molar in hexane) are added dropwise, and the mixture is warmed to 0° C. after 5 minutes and cooled again to −40° C. after 15 minutes. A solution of 0.70 g of ethyl 4-formylcinnamate in THF is added dropwise and, after 5 minutes, the reaction mixture is warmed to room temperature. The solvent is removed in a rotary evaporator. 0.75 g of product is obtained as an E/Z mixture.

Workup

  1. temperaturethe mixture is warmed to 0° C. after 5 minutes
  2. temperaturecooled again to −40° C. after 15 minutes
  3. temperaturethe reaction mixture is warmed to room temperature
  4. customThe solvent is removed in a rotary evaporator

Sources & evidence

ORD record
ord-6fe965fc47684100a91102a5f2795b52
Source dataset
uspto-grants-2009_03
Patent number
US07498460B2

Reaction notes

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