[4-(Tert-butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanol → [4-(tert-Butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanone

HRID 911709Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[OH:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

Add manganese dioxide (1.44 g) to a stirred solution of [4-(tert-butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanol (360 mg, 0.303 mmol) in anhydrous 1,4-dioxane (25 mL). Heat the mixture to 70° C. overnight. Cool the reaction mixture to room temperature, filter through Celite® and wash with EtOAc. Concentrate the filtrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (1:1) to provide the desired intermediate (233 mg, 65%). GC-MS m/z: 327 (M+).

Workup

temperatureCool the reaction mixture to room temperature
filtrationfilter through Celite®
washwash with EtOAc
concentrationConcentrate the filtrate in vacuo
customPurify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (1:1)

Sources & evidence

ORD record: ord-a43ddd5046c94edab278787ebb5d60fb
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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