Cesium carbonate → (R)-(2', 6'-dimethyl-4'-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol

HRID 2280630Notes

Reaction equation

CS([O:5][C@H:6]1[CH2:10][CH2:9][O:8][CH2:7]1)(=O)=O.[OH:11][CH2:12][C:13]1[CH:14]=[C:15]([C:19]2[C:24]([CH3:25])=[CH:23][C:22](O)=[CH:21][C:20]=2[CH3:27])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:25][C:24]1[CH:23]=[C:22]([O:5][C@@H:6]2[CH2:10][CH2:9][O:8][CH2:7]2)[CH:21]=[C:20]([CH3:27])[C:19]=1[C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][OH:11])[CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The crude (S)-tetrahydrofuran-3-yl methanesulfonate 2b (522 mg, 3.14 mmol), 3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-ol (714 mg, 3.13 mmol, prepared by a method disclosed in Chinese patent application CN101616913) and cesium carbonate (3.10 g, 9.39 mmol) were dissolved in 30 mL of N,N-dimethylformamide. The reaction mixture was heated to 80° C. and stirred for 12 hours. The resulting solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound (R)-(2′, 6′-dimethyl-4′-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol 2c (540 mg, yield 58.0%) as a colorless oil.

Workup

concentrationThe resulting solution was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record: ord-be86cd1c0ade40fe8dc3bdca2f1eb126
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139548B2

Reaction notes

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