4-(3-Hydroxyprop-1-ynyl)benzonitrile → 4-(3-Hydroxypropyl)benzonitrile
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][OH:12])=[CH:5][CH:4]=1)#[N:2]>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]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1)#[N:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A suspension of Compound 72-1 (5.79 g) and chlorotris(triphenylphosphine)rhodium(I) (5.00 g) in toluene (150 ml) was stirred under a hydrogen atmosphere at 65° C. for 15 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=99:1-50:50) to give the object product (4.20 g) as a brown oil.
Workup
- concentrationThe reaction mixture was concentrated
- additiondiisopropyl ether was added
- filtrationthe mixture was filtered through celite
- concentrationThe filtrate was concentrated
- customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-50:50)
Sources & evidence
- ORD record
- ord-5792507b202048c4882de0058a3f43a5
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129361B2
Reaction notes
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