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

HRID 1375270

反応式

HRID 1375270 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-fbc56e09fd9c4f768d0d3ffb2e79b34b
出典データセット
uspto-grants-2007_01
特許番号
US07166726B2

関連ノート

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