Carbon Dioxide → 1(5-Methyl-thien-2-yl) 3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

HRID 2609

反応式

HRID 2609 の反応式
[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=3)[C:10]([CH3:19])([CH3:18])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1.[Li]C(C)(C)C.CCCCC.CN([CH:33]=[O:34])C.C(=O)=O>C1COCC1.CCOCC>[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:33]=[O:34])[CH:15]=3)[C:10]([CH3:19])([CH3:18])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1

参加物

8

反応物 5

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 8003PentaneHCID 186200621-(5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene2 回HCID 178418306HCID 178418306、化合物

生成物 1

HCID 186200661(5-Methyl-thien-2-yl) 3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a cold (-78° C.) solution of 1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound F, 1.35 g, 4.1 mmol), in THF (20 mL) was added t-BuLi in pentane (1.7M solution, 3.5 mL, 5.95 mmol). The reaction was stirred for 15 minutes and DMF (600 mg, 5.8 mmol) was added and dry-ice cooling was replaced with ice-water bath. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with ether (70 mL) and washed with water (5 mL), brine (5 mL) and dried with MgSO4. Solvent was removed by distillation. The product was purified by silicagel chromatography to afford the title compound as a colorless oil.

後処理

  1. stirringThe mixture was stirred at ambient temperature for 4 hours
  2. washwashed with water (5 mL), brine (5 mL)
  3. dry with materialdried with MgSO4
  4. customSolvent was removed by distillation
  5. customThe product was purified by silicagel chromatography

出典と根拠

ORDレコード
ord-4955e9d4488f4c70a01e631513107eb7
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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