Methylenetriphenylphosphorane → [4-(5-Tert-butyl-4-isopropoxy-2-methyl-3-vinyl-phenylethynyl)-phenyl]acetic acid methyl ester

HRID 1765862Notes

Reaction equation

HRID 1765862 reaction equation
[CH2:1]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:21][O:22][C:23](=[O:50])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[C:32][C:33]2[CH:38]=[C:37]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:36]([O:43][CH:44]([CH3:46])[CH3:45])=[C:35]([CH:47]=O)[C:34]=2[CH3:49])=[CH:27][CH:26]=1>O1CCCC1>[CH3:21][O:22][C:23](=[O:50])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[C:32][C:33]2[CH:38]=[C:37]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:36]([O:43][CH:44]([CH3:45])[CH3:46])=[C:35]([CH:47]=[CH2:1])[C:34]=2[CH3:49])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 137960MethylenetriphenylphosphoraneHCID 60029385HCID 60029385, compound2×

Product 1

HCID 86600194[4-(5-Tert-butyl-4-isopropoxy-2-methyl-3-vinyl-phenylethynyl)-phenyl]acetic acid methyl esterYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methylidene triphenyl phosphorane [5 mL of 0.1M solution, 0.5 mmol, generated from methyl triphenylphosphonium bromide (2.5 g, 7 mmol) and 1.6M n-butyllithium solution in hexanes (2.9 mL, 4.7 mmol) in 50 mL of tetrahydrofuran] was added to a solution of [4-(5-tert-butyl-3-formyl-4-isopropoxy-2-methyl-phenylethynyl)-phenyl]-acetic acid methyl ester (Intermediate 144, 0.052 g, 0.13 mmol) in tetrahydrofuran (1 mL). After 1 h the reaction mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a clear oil that after flash column chromatography over silica gel (230–400 mesh) using 5% ethyl acetate in hexane as the eluent afforded the title compound (0.02 g, 39%).

Workup

  1. customAfter 1 h the reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to a clear oil that after flash column chromatography over silica gel (230–400 mesh)

Sources & evidence

ORD record
ord-df6ec9ee358f48f2a23febc1219a49eb
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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