Methyl 4-trimethylsilylethynylbenzoate → 4-(Trimethylsilylethynyl)benzyl alcohol

HRID 2405663

반응식

HRID 2405663 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:13][Si:12]([C:11]#[C:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1)([CH3:14])[CH3:15]

참가 물질

4

반응물 2

HCID 640161Methyl 4-trimethylsilylethynylbenzoateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 112411654-(Trimethylsilylethynyl)benzyl alcohol수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Under argon condition, 4-((trimethylsilyl)ethynyl)benzoic acid methyl ester (316 mg, 1.36 mmol) was dissolved in 5 mL of dry THF, and then cooled to 0° C., and LiAlH4 (2.04 mL, 1.0 M solution in THF, 2.04 mmol) was slowly added thereto. Upon completion of the reaction after stirring for 30 minutes at 0° C., the reaction was terminated by adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution and then 231 μL of water. When the white viscous precipitate was produced, the mixture was filtered through a silica pad to remove the precipitate. The resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 258 mg (1.26 mmol, 93%) of the desired compound.

후처리

  1. customUpon completion of the reaction
  2. customthe reaction was terminated
  3. additionby adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution
  4. customWhen the white viscous precipitate was produced
  5. filtrationthe mixture was filtered through a silica pad
  6. customto remove the precipitate
  7. concentrationThe resulting solution was concentrated by distillation under reduced pressure
  8. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-19996c85b8074865ab2da9e5ac55d734
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809012B2

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