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

HRID 368902Notes

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 and pyridinium-p-toluenesulfonate (70 g, 0.278mole) in ethanol (250 ml) is heated at 60° C. for 9 hours. The reaction mixture is concentrated in vacuo and co-evaporated with toluene. The residue is diluted with toluene and the resulting solid is removed by filtration. The filtrate is evaporated under reduced pressure to give the crude 6a as light brown oil.

Workup

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

Sources & evidence

ORD record: ord-1c31d263e8cc4dd5a90395ad0d84a24e
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133485

Reaction notes

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