Acetonitrile → HCID 67958805, 화합물

HRID 2280424노트

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HRID 2280424 반응식
[C:1](#[N:3])[CH3:2].C([Li])CCC.[Si:9]([O:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>C1COCC1>[Si:9]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:22](=[O:23])[CH2:2][C:1]#[N:3])=[CH:25][CH:26]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 12018889HCID 12018889, 화합물HCID 178418339Butyllithium

생성물 1

HCID 67958805HCID 67958805, 화합물수율 24%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a chilled (−78° C.) solution of acetonitrile (MeCN) (1.13 mL, 4 equiv) in THF (54 mL) was added butyllithium (BuLi) (1.62 mL, 10 M in hexanes, 3 equiv) dropwise, keeping the temperature under −60° C. The mixture was stirred for 15 minutes at −78° C. A solution of 4-(((tert-butyldimethylsilyl)oxy)methyl)benzoyl chloride (1.44 g) in THF (5 mL) was slowly added, and the reaction mixture was stirred at −78° C. for 45 minutes. The reaction was then quenched with aqueous ammonium chloride and diluted with EtOAc. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate, and concentrated onto silica gel. Purification by silica chromatography (9:1 hexanes:EtOAc to EtOAc) provided the title compound (370 mg, 24% yield) and the de-silylated product (330 mg).

후처리

  1. customunder −60° C
  2. stirringthe reaction mixture was stirred at −78° C. for 45 minutes
  3. customThe reaction was then quenched with aqueous ammonium chloride
  4. additiondiluted with EtOAc
  5. customThe phases were separated
  6. washthe organic phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated onto silica gel
  9. customPurification by silica chromatography (9:1 hexanes:EtOAc to EtOAc)

출처 및 근거

ORD 기록
ord-12f07227daa3472baedd850ab3c8581a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139532B2

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