Dimethyl Sulfoxide → 5-((tert-Butyldimethylsilyl)oxy)pentanal

HRID 748780ノート

反応式

HRID 748780 の反応式
CS(C)=O.C(N(CC)CC)C.[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Cl-].[NH4+]>CCCCCC.ClCCl>[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[O:25])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 36143185-((Tert-butyldimethylsilyl)oxy)pentan-1-ol

生成物 1

HCID 109877035-((tert-Butyldimethylsilyl)oxy)pentanal収率 81.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

Under a nitrogen atmosphere and at 0° C., dimethylsulfoxide (7.81 ml, 110 mmol), triethylamine (9.60 ml, 69.0 mmol), and a sulfur trioxide-pyridine complex (4.39 g, 27.6 mmol) were added to a dichloromethane solution (80 ml) of 5-(t-butyldimethylsilyloxy)pentanol (3.00 g, 13.8 mmol). The resulting mixture was stirred at 0° C. for 30 minutes and then, at room temperature for further 3 hours. After cooling to 0° C., a saturated aquoeus ammonium chloride solution was added. Dichloromethane was distilled off under reduced pressure. To the residue was added ethyl acetate. After the water layer was separated, the organic layer was washed with water and brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was subjected to chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=20:1 eluate was concentrated, whereby the title compound (2.42 g, 11.2 mmol, 81%) was obtained as a colorless oil.

後処理

  1. waitat room temperature for further 3 hours
  2. temperatureAfter cooling to 0° C.
  3. distillationDichloromethane was distilled off under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. customAfter the water layer was separated
  6. washthe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue thus obtained
  10. concentrationethyl acetate=20:1 eluate was concentrated

出典と根拠

ORDレコード
ord-c59df5db453846e3b9ec2d2902daf54c
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

反応ノート

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