3-(3-Chloro-2-methylphenyl)prop-2-yn-1-ol → 3-(3-Chloro-2-methylphenyl)-1-propanol

HRID 1093411Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([C:8]#[C:9][CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([CH2:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of Compound 54-1 (2.58 g) and chlorotris(triphenylphosphine)rhodium(I) (1.50 g) in toluene (80 ml) was stirred under a hydrogen atmosphere at 60° C. for 11 hr. The reaction mixture was filtered through celite and concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20) to give the object product (2.11 g) as a brown oil.

Workup

filtrationThe reaction mixture was filtered through celite
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20)

Sources & evidence

ORD record: ord-2f678ef4754d4b2eb09a80553d20bc57
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129361B2

Reaction notes

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