2-(tert-Butyldimethylsilyloxymethyl)-5-(1-hydroxy-3-methyl-butyl)-pyridine → 2-(tert-Butyldimethylsilyloxymethyl)-5-(3-methyl-butyryl)-pyridine

HRID 2041575Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

Add manganese dioxide (1.32 g) to a stirred solution of 2-(tert-butyldimethylsilyloxymethyl)-5-(1-hydroxy-3-methyl-butyl)-pyridine (330 mg, 1.066 mmol) in anhydrous 1,4-dioxane (30 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 to provide the desired intermediate as oil (327 mg, 100%). GC-MS m/z: 307 (M+.).

Workup

temperatureCool the reaction mixture to room temperature
filtrationfilter through Celite®
washwash with EtOAc
concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record: ord-7fe06885d9b84d9b93af96cca6611874
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580780B2

Reaction notes

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