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

HRID 1412454
Notes
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Reaction equation

HRID 1412454 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 222444231-{[(Tert-butyldimethylsilyl)oxy]methyl}cyclobutane-1-carbaldehydeHCID 178418573HCID 178418573, compound2×

Product 1

HCID 670086071-[1-({[Tert-butyl(dimethyl)silyl]oxy}methyl)cyclobutyl]ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-320b223249a646deb9389f77a6ccdb29
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921379B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes