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

HRID 2620

反応式

HRID 2620 の反応式
[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

参加物

7

反応物 3

HCID 6228DimethylformamideHCID 861915082,2-Dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene2 回HCID 178418306HCID 178418306、化合物

生成物 1

HCID 1317205762,2-Dimethyl-4(5-methyl-thien-2-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(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.

後処理

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

出典と根拠

ORDレコード
ord-9f2a11bfe87a4bf99972d2587a25f59f
出典データセット
uspto-grants-1998_03
特許番号
US05728846

関連ノート

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