Dimethylformamide → 2,2-Dimethyl-4(tol4-yl)-chrom-3-en-6-al

HRID 2616

反応式

HRID 2616 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)[O:3]1.[Li]C(C)(C)C.CN([CH:29]=[O:30])C>C1COCC1.CCCCC.C(OCC)(=O)C>[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)[O:3]1

参加物

7

反応物 3

HCID 6228DimethylformamideHCID 158872872,2-Dimethyl-4(tol-4-yl)-6-bromo-chrom-3-ene2 回HCID 178418306HCID 178418306、化合物

生成物 1

HCID 158872882,2-Dimethyl-4(tol4-yl)-chrom-3-en-6-al

試薬・触媒・溶媒 3

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a cold (-78° C.) solution of 2,2-dimethyl-4(tol-4-yl)-6-bromo-chrom-3-ene (Compound P, 480 mg, 1.45 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 1.1 mL) and the mixture was stirred for 30 minutes. DMF (200 mg, 2.9 mmol) was added, the mixture was warmed to ambient temperature and stirred for 3 hours. The reaction 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.

後処理

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

出典と根拠

ORDレコード
ord-6d1ee6ee5f4248aba938c037e104dcfb
出典データセット
uspto-grants-1998_03
特許番号
US05728846

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