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

HRID 1408686노트

반응식

HRID 1408686 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-77cd90b966a946899a16679c22503d4c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921359B2

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