Dimethylformamide → 2,2-Dimethyl-4(tol-4-yl)-thiochrom-3-en-6-al

HRID 2288308

反応式

HRID 2288308 の反応式
[CH3:1][C:2]1([CH3:20])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7](Br)[CH:8]=2)[S:3]1.[Li]CCCC.CN([CH:29]=[O:30])C>C1COCC1.CCCCCC>[CH3:1][C:2]1([CH3:20])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:29]=[O:30])[CH:8]=2)[S:3]1

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 861914872,2-Dimethyl-4(tol-4-yl)-6-bromo-thiochrom-3-ene2 回HCID 178418339Butyllithium

生成物 1

HCID 158872822,2-Dimethyl-4(tol-4-yl)-thiochrom-3-en-6-al

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-10 °C

実験手順

To a cold (-78° C.) solution of 2,2-dimethyl-4(tol-4-yl)-6-bromo-thiochrom-3-ene (Compound N, 280 mg, 0.81 mmol) in THF (5 mL) was added n-BuLi in hexane (1.6 M solution, 0.66 mL). The mixture was gradually warmed to -10° C. over 25 min. and recooled to -78° C. To this solution was added DMF (80 mg, 1.1 mmol) and stirred at ambient temperature for 5 hours. The reaction was quenched by adding water (10 mL), ethyl acetate (100 mL), and the organic layer was washed with brine (10 mL), dried and the solvent removed by distillation. The crude material was used in the next reaction without further purification.

後処理

  1. customrecooled to -78° C
  2. customThe reaction was quenched
  3. additionby adding water (10 mL), ethyl acetate (100 mL)
  4. washthe organic layer was washed with brine (10 mL)
  5. customdried
  6. customthe solvent removed by distillation
  7. customThe crude material was used in the next reaction without further purification

出典と根拠

ORDレコード
ord-dc2a6349e3fa4cfc88f7dfc7b7be2995
出典データセット
uspto-grants-2000_07
特許番号
US06087505

関連ノート

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