Acetonitrile → HCID 67958805、化合物

HRID 2280424ノート

反応式

HRID 2280424 の反応式
[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]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 12018889HCID 12018889、化合物HCID 178418339Butyllithium

生成物 1

HCID 67958805HCID 67958805、化合物収率 24%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-12f07227daa3472baedd850ab3c8581a
出典データセット
uspto-grants-2015_09
特許番号
US09139532B2

反応ノート

読み込み中…