Hydrochloric Acid → 4-(5-Bromoindolin-1-yl)cyclohexanone

HRID 1922515ノート

反応式

HRID 1922515 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]1)[CH2:6][CH2:5]2.Cl>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]1)[CH2:6][CH2:5]2

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 585053135-Bromo-1-(1,4-dioxaspiro[4.5]decan-8-yl)indoline

生成物 1

HCID 598070744-(5-Bromoindolin-1-yl)cyclohexanone収率 83.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of compound 4 (4.0 g, 11.83 mmol) in acetone (50 mL) was treated with 10% HCl solution (50 mL) and the resulting mixture was stirred for over night (16 h). Acetone was evaporated, crude was basified with 2 N NaOH solution and product was extracted into CH2Cl2 (3×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and the crude product was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:4) to obtain compound 5 (2.9 g, 83%) as a solid. 1H NMR (CDCl3) δ 7.15 (d, J=6.6 Hz, 2H), 6.32 (d, J=8.7 Hz, 1H), 3.81 (tt, J=7.2, 23.4 Hz, 1H), 3.37 (t, J=16.8 Hz, 2H), 2.95 (t, J=16.5 Hz, 2H), 2.51-2.41 (m, 4H), 2.18-2.11 (m, 2H), 1.92-1.78 (m, 2H). MS-ESI (m/z, %): 296 (96), 294 (M+, 100), 200 (30).

後処理

  1. customAcetone was evaporated
  2. extractionwas extracted into CH2Cl2 (3×25 mL)
  3. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe crude product was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:4)

出典と根拠

ORDレコード
ord-dc6c85701d9e4229b65649a5c22abca5
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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