Dimethylformamide → 2,2-Dimethyl-4(5-methyl-thien-2-yl)-chrom-3-en-6-al

HRID 2620

반응식

HRID 2620 반응식
[CH3:1][C:2]1([CH3:19])[CH:11]=[C:10]([C:12]2[S:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7](Br)[CH:8]=2)[O:3]1.[Li]C(C)(C)C.CN([CH:28]=[O:29])C>C1COCC1.CCCCC.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:19])[CH:11]=[C:10]([C:12]2[S:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:28]=[O:29])[CH:8]=2)[O:3]1

참가 물질

7

반응물 3

HCID 6228DimethylformamideHCID 861915082,2-Dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene2회HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 1317205762,2-Dimethyl-4(5-methyl-thien-2-yl)-chrom-3-en-6-al

시약·촉매·용매 3

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a cold (-78° C.) solution of 2,2-dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene (Compound R, 1.2 g, 3.6 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 2.3 mL). After 30 minutes, DMF (465 mg, 5 mmol) was added and the mixture was allowed to warm to ambient temperature and stirred for 3 hours. The mixture was diluted with ethyl acetate (150 mL), washed with brine (10 mL), dried and the solvent was removed by evaporation. Purification by chromatography on silica gel column gave the title compound as a colorless oil.

후처리

  1. washwashed with brine (10 mL)
  2. customdried
  3. customthe solvent was removed by evaporation
  4. customPurification by chromatography on silica gel column

출처 및 근거

ORD 기록
ord-9f2a11bfe87a4bf99972d2587a25f59f
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728846

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