Hydrochloric Acid → 6-Bromospiro[chroman-2,1'-cyclopentan]-4-one

HRID 1408686ノート

反応式

HRID 1408686 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[C:12]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13]1.N1CCCC1.Cl>CO.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:12]1([CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9][C:8]2=[O:10]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8452CyclopentanoneHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

生成物 1

HCID 591678716-Bromospiro[chroman-2,1'-cyclopentan]-4-one収率 110.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (15.8 g, 73.8 mmol), cyclopentanone (12.35 g, 147 mmol) and pyrrolidine (12 mL, 140 mmol) in MeOH (300 mL) was stirred at room temperature overnight. The mixture was concentrated in vacuo to give the residue, which was added water and HCl (36%) until pH=1. The mixture was extracted with EtOAc and then the organic layer was concentrated to give 6-bromospiro[chroman-2,1′-cyclopentan]-4-one (23 g, 100%). 1H-NMR (CDCl3): 1.64 (m, 4H), 1.72 (m, 2H), 2.03 (m, 2H), 2.78 (s, 2H), 6.78 (m, 1H), 7.48 (m, 1H), 7.91 (m, 1H).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give the residue, which
  3. extractionThe mixture was extracted with EtOAc
  4. concentrationthe organic layer was concentrated

出典と根拠

ORDレコード
ord-77cd90b966a946899a16679c22503d4c
出典データセット
uspto-grants-2014_12
特許番号
US08921359B2

反応ノート

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