Benzaldehyde → 1-Phenyl-3-(trimethylsilyl)-2-propyn-1-ol

HRID 1588717

반응식

HRID 1588717 반응식
C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].[CH:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OCC)C>O1CCCC1.O>[CH3:11][Si:12]([C:15]#[C:16][CH:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:24])([CH3:14])[CH3:13]

참가 물질

7

반응물 4

HCID 240BenzaldehydeHCID 3283Diethyl EtherHCID 66111TrimethylsilylacetyleneHCID 57426343Lithium bis(trimethylsilyl)amide

생성물 1

HCID 27604161-Phenyl-3-(trimethylsilyl)-2-propyn-1-ol

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Place lithium hexamethyldisilazane (12 mL of a IM solution in tetrahydrofuran, 12 mmol) under an argon atmosphere and cool to 0° C. Add trimethylsilylacetylene (1.7 mL, 12 mmol) and stir for 1 hour at 0° C. Add benzaldehyde (1.06 g, 10 mmol) in tetrahydrofuran (25 mL). Allow to warm to room temperature and stir for 3 hours. Pour the mixture into ethyl ether and water, separate the organic phase and evaporate the solvent in vacuo. Filter the oil through silica gel (20% ethyl acetate/hexane) and evaporate the solvent in vacuo to yield the title compound.

후처리

  1. customseparate the organic phase
  2. customevaporate the solvent in vacuo
  3. filtrationFilter the oil through silica gel (20% ethyl acetate/hexane)
  4. customevaporate the solvent in vacuo

출처 및 근거

ORD 기록
ord-fa6f0d3aed2a43f7a7782b5724257895
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05223518

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