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

HRID 368893Notes

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 compound 5a, (3S)-2-(2,4-Difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-1-butene, (81 g, 0.302 mole) and pyridinium-p-toluenesulfonate (32.7 g, 0.130 mole) in 1200 ml of ethanol was heated at 60° C. for 9 hours. The reaction mixture was concentrated in vacuo and co-evaporated with toluene. Toluene was then added to the residue and the resulting solid was removed by filtration. The filtrate was evaporated under reduced pressure and the residue was chromatographed on silica gel. Elution with 10% ethyl acetate in hexane gave the title compound 6a as light yellow oil (44.96 g, 81%)

Workup

concentrationThe reaction mixture was concentrated in vacuo and co-evaporated with toluene
additionToluene was then added to the residue
customthe resulting solid was removed by filtration
customThe filtrate was evaporated under reduced pressure
customthe residue was chromatographed on silica gel
washElution with 10% ethyl acetate in hexane

Sources & evidence

ORD record: ord-267a63ca5d244e4ea135e0d1b038dd2d
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133485

Reaction notes

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