tert-Butyldimethylsilyl chloride → 1-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-ol

HRID 633387

반응식

HRID 633387 반응식
[CH3:1][C:2]([OH:6])([CH3:5])[CH2:3][OH:4].[CH3:7][C:8]([Si:11](Cl)([CH3:13])[CH3:12])([CH3:10])[CH3:9]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:8]([Si:11]([CH3:13])([CH3:12])[O:4][CH2:3][C:2]([CH3:5])([OH:6])[CH3:1])([CH3:10])([CH3:9])[CH3:7]

참가 물질

5

반응물 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 684102-Methylpropane-1,2-diol

생성물 1

HCID 189346221-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-ol수율 84%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

2-Methylpropane-1,2-diol (1.08 g, 12.0 mmol, 1.0 equiv) in DCM (40 mL) under argon was cooled to 0° C. TEA (2.50 mL, 18.0 mmol, 1.5 equiv), DMAP (75.0 mg, 0.600 mmol, 0.05 equiv), and TBSCl (2.00 g, 13.2 mmol, 1.1 equiv) were added sequentially, and the reaction was allowed to warm up to ambient temperature overnight. Complete conversion of reactant to product was confirmed by TLC eluted with EtOAc and visualized with KMnO4. The solvent was removed in vacuo, and the residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc 2×, and the combined organics were dried with Na2SO4, filtered, and concentrated to provide 1-(tertbutyldimethylsilyloxy)-2-methylpropan-2-ol (2.05 g, 84%) as a light brown oil that was used without further purification.

후처리

  1. washeluted with EtOAc
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc 2×
  5. dry with materialthe combined organics were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ec92d2b197034b40b36cef6e6ddb730f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321763B2

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