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

HRID 368897Notes

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 5b, (3R)-2-(2,4-Difluorphenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-1-butene, (40 g, 0.149 mole) and pyridinium-p-toluenesulfonate (24.61 g, 0.098 more) in 400 ml of ethanol was heated at 60° C. for 14.5 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 6b as light yellow oil (14.68 g, 53%).

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-c51ddbc748bd4ef79880da546cc23e9f
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133485

Reaction notes

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