Ammonium Chloride → 1-[1-({[Tert-butyl(dimethyl)silyl]oxy}methyl)cyclobutyl]ethanol

HRID 2048481Notes

Reaction equation

[CH3:1][Mg]Br.[Si:4]([O:11][CH2:12][C:13]1([CH:17]=[O:18])[CH2:16][CH2:15][CH2:14]1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].[Cl-].[NH4+]>O1CCCC1>[Si:4]([O:11][CH2:12][C:13]1([CH:17]([OH:18])[CH3:1])[CH2:14][CH2:15][CH2:16]1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Methylmagnesium bromide (21 mL, 1.0 M tetrahydrofuran solution) was cooled to 0° C., a solution of 1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclobutanecarbaldehyde (4.0 g) in tetrahydrofuran (40 mL) was added dropwise, and the mixture was stirred at 0° C. for 1 hr. Methylmagnesium bromide (10 mL, 1.0 M tetrahydrofuran solution) was added, and the mixture was stirred at 0° C. for 30 min. The reaction mixture was added to saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as an oily compound (2.5 g, 58%).

Workup

stirringthe mixture was stirred at 0° C. for 30 min
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-689babc7968c425ca70282a26839688a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592431B2

Reaction notes

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