Dimethylformamide → 3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-2,4-dimethoxy-benzaldehyde

HRID 488825ノート

反応式

HRID 488825 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]3([CH3:23])[CH3:22])[C:7]=1[O:8][CH3:9].CN(C)[CH:28]=[O:29]>C1COCC1>[CH3:21][C:16]1([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]2[CH:11]=[C:10]([C:6]3[C:7]([O:8][CH3:9])=[C:2]([CH:3]=[CH:4][C:5]=3[O:24][CH3:25])[CH:28]=[O:29])[CH:19]=[CH:18][C:17]1=2

参加物

4

反応物 2

HCID 6228DimethylformamideHCID 694617116-(5-Bromo-2,6-dimethoxyphenyl)-1,1,4,4-tetramethy-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 222683493-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-2,4-dimethoxy-benzaldehyde収率 72.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 6-(5-bromo-2,6-dimethoxyphenyl)-1,1,4,4-tetramethy-1,2,3,4-tetrahydronaphthlene (0.24 g, 0.55 mmol) in anhydrous THF (6 mL) was added at −78° C. under argon n-BuLi (1.6 M in hexane, 0.7 mL, 1.1 mmol). The solution was stirred for 5 minutes at −78° C. and N,N-dimethylformamide (0.13 mL, 1.65 mmol) was added. The reaction mixture was stirred 2 hours at −78° C. then quenched with aqueous ammonium chloride and brought to room temperature. The solution was diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was chromatographed and silica gel (eluent: ethyl acetate/hexane, 1:9) to give 0.14 g (72%) of 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-2,4-dimethoxy-benzaldehyde. 1H NMR (500 MHz; CDCl3): δ 1.29 (s, 6 H); 1.32 (s, 6 H); 1.72 (s, 4 H); 3.37 (s, 3 H); 383 (s, 3 H); 6.83 (d, J=9.0 Hz, 1 H); 7.14 (dd, J1=2.0 Hz, J2=8.5 Hz, 1 H); 7.33 (d, J=8.0 Hz, 1 H); 7.36 (s, 1 H); 7.85 (d, J=8.5 Hz, 1 H); 10.29 (s, 1 H).

後処理

  1. stirringThe reaction mixture was stirred 2 hours at −78° C.
  2. customthen quenched with aqueous ammonium chloride
  3. custombrought to room temperature
  4. additionThe solution was diluted with ethyl acetate
  5. washwashed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed

出典と根拠

ORDレコード
ord-fc07daa893be4dd19c8a9e7640b2c8ac
出典データセット
uspto-grants-2005_12
特許番号
US06974826B2

反応ノート

読み込み中…