Methyl 3,3-bis[(tert-butyldimethylsiloxy)methyl]acrylate → 3,3-Bis[(tert-butyldimethylsiloxy)methyl]-2-propen-1-ol

HRID 363498

反応式

HRID 363498 の反応式
[O:1]([CH2:9][C:10]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:11][C:12](OC)=[O:13])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[O:17]([CH2:16][C:10]([CH2:9][O:1][Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:4])=[CH:11][CH2:12][OH:13])[Si:18]([C:21]([CH3:23])([CH3:22])[CH3:24])([CH3:20])[CH3:19]

参加物

4

反応物 2

HCID 10833281Methyl 3,3-bis[(tert-butyldimethylsiloxy)methyl]acrylateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 107363853,3-Bis[(tert-butyldimethylsiloxy)methyl]-2-propen-1-ol収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 5a (11.24 g, 30 mmol) in CH2Cl2 (100 mL) was cooled to -60° C. and treated dropwise with a solution of diisobutylaluminum hydride in CH2Cl2 (1.0M, 40 mL). The reaction mixture was quenched with saturated potassium sodium tartrate tetrahydrate and warmed to room temperature. The aqueous layer was extracted with CH2Cl2, and the combined organic layer was washed with water and brine. The organic layer was dried (NaSO4) and concentrated. The residue was purified by flash column chromatography over silica gel with hexane:EtOAc (5:1) as eluant to give 6a (9.77 g, 94%) as an oil: IR (neat) 3357, 1471 cm-1 ; 1H NMR (CDCl3) δ 0.05 and 0.06 (s, 6 H, SiCH3), 0.88 and 0.89 (s, 9 H, C(CH3)3), 1.86 (br s, 1 H, OH), 4.14 (br s, 2 H, CH2OH), 4.20 (m, 4 H, CH2OSi), 5.80 (m, 1 H, =CH); 13C NMR (CDCl3) δ -1.95, 18.19, 18.33, 25.62, 25.79, 25.88, 58.50, 59.24, 64.75, 125.47, 140.81. Anal. Calcd for C17H38O3Si2 : C, 58.90; H: 11.05. Found: C, 59.00; H, 11.00.

後処理

  1. customThe reaction mixture was quenched with saturated potassium sodium tartrate tetrahydrate
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washthe combined organic layer was washed with water and brine
  4. dry with materialThe organic layer was dried (NaSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography over silica gel with hexane:EtOAc (5:1) as eluant

出典と根拠

ORDレコード
ord-fe651c90b79c435e9dd1cea156894f5a
出典データセット
uspto-grants-1999_02
特許番号
US05874464

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