Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2S)-3-(2,4-Difluorophenyl)-3-buten-2-ol

HRID 368900Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C@@H:11]([O:13]C1CCCCO1)[CH3:12])=[CH2:10].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:10])[C@@H:11]([OH:13])[CH3:12]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of crude 5a, (870) and pyridinium-p-toluenesulfonate (350 g, 1.39 mole) in ethanol (12 L) was heated at 60° C. for 9 hours. The reaction mixture was concentrated in vacuo and co-evaporated with toluene. The residue was diluted with toluene and the resulting solid was removed by filtration. The filtrate was evaporated under reduced pressure to give the crude 6a as light brown oil (664 g).

Workup

concentrationThe reaction mixture was concentrated in vacuo and co-evaporated with toluene
additionThe residue was diluted with toluene
customthe resulting solid was removed by filtration
customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-488496685dd2454d8cea391c9d8d1979
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133485

Reaction notes

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