2'-fluoro-5'-methoxy-2-(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)biphenyl-4-ol → 2'-fluoro-5'-methoxy-2-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)biphenyl-4-ol

HRID 1049591Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[C:17]1[CH2:18][C:19]([CH3:26])([CH3:25])[O:20][C:21]([CH3:24])([CH3:23])[CH:22]=1>CO.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[CH:17]1[CH2:18][C:19]([CH3:26])([CH3:25])[O:20][C:21]([CH3:24])([CH3:23])[CH2:22]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2′-fluoro-5′-methoxy-2-(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)biphenyl-4-ol (124 mg) in methanol (3 mL) was added 20% palladium hydroxide (28 mg) and, under a hydrogen atmosphere, the mixture was stirred at 60° C. for 3 hr. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to give a crude product of the title compound as a colorless oil. This compound was used for the next step without further purification.

Workup

filtrationThe reaction mixture was filtered
customthe solvent of the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-b75b20f88236440db05d154ac7d965a1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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