Benzyl Chloride → 1-Benzyl-5-fluoro-1H-indole

HRID 5601

反応式

HRID 5601 の反応式
C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].[F:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[CH:29]2.[CH2:35](Cl)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CCOCC.O>[CH2:35]([N:31]1[C:32]2[C:28](=[CH:27][C:26]([F:25])=[CH:34][CH:33]=2)[CH:29]=[CH:30]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

7

反応物 4

HCID 7503Benzyl ChlorideHCID 2855718-Crown-6HCID 678615-FluoroindoleHCID 23665647Potassium tert-butoxide

生成物 1

HCID 197966391-Benzyl-5-fluoro-1H-indole収率 14.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒3 回

実験手順

To a solution of 0.8 g (3.03 mmoles) of 18-crown-6 in 100 ml of dry ether was added 3.27 g (29.14 mmoles) of potassium tert-butoxide. The mixture was stirred while a solution of 3.75 g (27.75 mmoles) of 5-fluoroindole in 80 ml of ether was added. The stirring was continued for 0.5 hour. Solid was present. Then 3.69 g (29.15 mmoles) of benzyl chloride in 80 ml of ether was added. The mixture was stirred for 28 hours. Water (100 ml) was added. The layers were separated. The aqueous layer was extracted with 100 ml of ether. The combined ether layers were washed with 50 ml of brine and dried over MgSO4. Evaporation of the solvent left 6.95 g of orange oil. The oil was chromatographed on a 600 g column of silica gel. The column was eluted with 30% CH2Cl2 -Skellysolve B and 200 ml fractions were collected. The fractions were assayed by silica gel tlc (1×4") (30% CH2Cl1 -Skellysolve B). Fractions 11-15 were combined giving 0.88 g (14%) of 1-benzyl-5-fluoroindole as a pale yellow oil which contained a small amount of 1,3-dibenzyl-5-fluorindole.

後処理

  1. additionwas added
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with 100 ml of ether
  4. washThe combined ether layers were washed with 50 ml of brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. waitleft 6.95 g of orange oil
  8. customThe oil was chromatographed on a 600 g column of silica gel
  9. washThe column was eluted with 30% CH2Cl2 -Skellysolve B and 200 ml fractions
  10. customwere collected

出典と根拠

ORDレコード
ord-d0c9152d9e564c87bc2c916dccd31853
出典データセット
uspto-grants-1993_09
特許番号
US05245046

関連ノート

読み込み中…