Bromochloromethane → 5,6-Methylenedioxy-1-tetralone

HRID 847264ノート

反応式

HRID 847264 の反応式
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13].[C:14](=O)([O-])[O-].[Cs+].[Cs+].BrCCl>CN(C=O)C>[CH2:14]1[O:12][C:11]2[C:2](=[C:3]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:13])[CH2:6][CH2:5][CH2:4]3)[O:1]1

参加物

5

反応物 3

HCID 6333BromochloromethaneHCID 10796Cesium carbonateHCID 123536405,6-Dihydroxy-3,4-dihydronaphthalen-1(2H)-one

生成物 1

HCID 111168225,6-Methylenedioxy-1-tetralone収率 93.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of the product of Example 177 (30 g) in DMF (390 ml) was added cesium carbonate (83 g) followed by bromochloromethane (33 g) and the resulting mixture heated to 100° C. and mechanically stirred for 2 hours. The reaction was cooled, filtered and the solids washed with ethyl acetate. The filtrate concentrated and the residue taken up into water and toluene. The layers were separate and the aqueous layer reextracted with toluene. The extracts were combined, dried (MgSO4), filtered, treated with charcoal, refiltered and concentrated to provide 29.9 g of the desired product, m.p. 132°-136° C.

後処理

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washthe solids washed with ethyl acetate
  4. concentrationThe filtrate concentrated
  5. customThe layers were separate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. additiontreated with charcoal
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-2b28ac7ff6384383ade68b3f401ce490
出典データセット
uspto-grants-1992_08
特許番号
US05140040

反応ノート

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