Carbon Dioxide → 1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

HRID 2605

反応式

HRID 2605 の反応式
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([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:3][CH:2]=1.[Li]C(C)(C)C.CCCCC.CN(C)[CH:33]=[O:34].C(=O)=O>C1COCC1.C(OC(=O)C)C>[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([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:3][CH:2]=1

参加物

8

反応物 5

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 8003PentaneHCID 106876226-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene2 回HCID 178418306HCID 178418306、化合物

生成物 1

HCID 865886771-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a cold (-78° C.), stirred solution of 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B 1 g, 3.2 mmol), in THF (17 mL) was added t-BuLi in pentane (1.7M solution, 3 mL, 5.1 mmol). After 10 minutes dry dimethylformamide (DMF) (600 mg, 8 mmol) was added and the dry-ice cooling was replaced with ice-water bath. The mixture was gradually warmed to ambient temperature and diluted with ethylacetate (150 mL), washed with water (15 mL). The organic layer was dried with MgSO4 and solvent was removed under reduced pressure. The crude material was purified by silicagel chromatography to afford the title compound as a white solid.

後処理

  1. washwashed with water (15 mL)
  2. dry with materialThe organic layer was dried with MgSO4 and solvent
  3. customwas removed under reduced pressure
  4. customThe crude material was purified by silicagel chromatography

出典と根拠

ORDレコード
ord-bf0cea00f0c14b87bedbeafd627d9061
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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