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

HRID 2377475Notes

Reaction equation

HRID 2377475 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-1f84280686d14d79b0c2e3f7f1c69006
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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