p-Bromoacetophenone → Dimethylhydroxymethyl-4-acetylphenylacetylene

HRID 1095233Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])C)=C[CH:3]=1.N1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH3:17][C:18]([OH:22])(C#C)C.[Cl-].[NH4+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][C:13]1[C:2]([CH3:3])=[C:7]([C:6]#[C:5][CH2:8][OH:10])[CH:16]=[CH:15][C:14]=1[C:18](=[O:22])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

A 30 mL Schlenk tube was replaced with Ar, 1.59 g (8 mmol) of p-bromoacetophenone, 92.4 mg (0.08 mmol) of tetrakis(triphenylphosphine)palladium, 8 mL of piperidine and 853 μL (8.8 mmol) of 2-methyl-3-butyn-2-ol were added and the mixture was stirred at 100° C. for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and then the mixture was extracted with diethyl ether. The extract was dried over magnesium sulfate, followed by distilling off of the solvent under reduced pressure by an evaporator. The resulting crude reaction product was purified by column chromatography (Hexane/AcOEt=5/1) using silica gel to give dimethylhydroxymethyl-4-acetylphenylacetylene, i.e., the desired compound as a viscous yellow liquid. Yield: 1.5 g (yield: 93%).

Workup

additionwere added
extractionthe mixture was extracted with diethyl ether
dry with materialThe extract was dried over magnesium sulfate
distillationby distilling off of the solvent under reduced pressure by an evaporator
customThe resulting crude reaction product
customwas purified by column chromatography (Hexane/AcOEt=5/1)

Sources & evidence

ORD record: ord-aa13f0269cfd429f9620b982f48e88f1
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08137821B2

Reaction notes

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