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

HRID 1862739

반응식

HRID 1862739 반응식
[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

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 861914872,2-Dimethyl-4(tol-4-yl)-6-bromo-thiochrom-3-ene2회HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7370a2f5e78e461fae76995d32e9ea9e
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06538149B1

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