3-(4-Chloro-3-methylphenyl)-2-propyne-1-ol → HCID 59407589, compound

HRID 1093447Notes

Reaction equation

HRID 1093447 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][OH:11])=[CH:4][C:3]=1[CH3:12]>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[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][C:3]=1[CH3:12]

Participants

4

Reactant 1

HCID 594078283-(4-Chloro-3-methylphenyl)-2-propyne-1-ol

Product 1

HCID 59407589HCID 59407589, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of Compound 67-1 (3.08 g) and chlorotris(triphenylphosphine)rhodium(I) (3.00 g) in toluene (70 ml) was stirred under a hydrogen atmosphere at 65° C. for 11 hr. The reaction mixture was concentrated, diisopropyl ether was added and the mixture was filtered through celite. The filtrate was concentrated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-75:25) to give the object product (2.49 g) as a brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiisopropyl ether was added
  3. filtrationthe mixture was filtered through celite
  4. concentrationThe filtrate was concentrated
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-75:25)

Sources & evidence

ORD record
ord-99bf61a229494d0ca58b88c8c097e11f
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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