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

HRID 1412454ノート

反応式

HRID 1412454 の反応式
[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]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 222444231-{[(Tert-butyldimethylsilyl)oxy]methyl}cyclobutane-1-carbaldehydeHCID 178418573HCID 178418573、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-320b223249a646deb9389f77a6ccdb29
出典データセット
uspto-grants-2014_12
特許番号
US08921379B2

反応ノート

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