Dimethylformamide → 4-(Tert-butyldiphenylsilyloxymethyl)-3-methylbenzaldehyde

HRID 584213Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH3:27])[CH:3]=1.C([Li])CCC.CN(C)[CH:35]=[O:36].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Si:10]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:35]=[O:36])=[CH:3][C:4]=1[CH3:27])([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 1-bromo-4-(tert-butyldiphenylsilyloxymethyl)-3-methylbenzene (2.19 g) in tetrahydrofuran (30 ml) was added 1.6 M butyllithium in hexane (4.69 ml) by syringe under nitrogen atmosphere at −78° C. After 30 minutes of stirring at −78° C., N,N-dimethylformamide (1.16 ml) was added to the solution at −78° C. and then the mixture was allowed to warm to 5° C. over 1.5 hours. Saturated ammonium chloride solution (10 ml) was added to the mixture and the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give 4-(tert-butyldiphenylsilyloxymethyl)-3-methylbenzaldehyde (1.90 g) as a colorless oil.

Workup

temperatureto warm to 5° C. over 1.5 hours
customthe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate
extractionThe combined extract
washwas washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-dbd503d70030487b83e01f727d4a039e
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924278B2

Reaction notes

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