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

HRID 368904Notes

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 5b, and pyridinium-p-toluenesulfonate (17.5 g, 0.07 mole) in ethanol (500 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 6b 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-ec2cc1cd88a54badb165203fb7198ee0
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133485

Reaction notes

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