Hydrochloric Acid → HCID 58424073, compound

HRID 1408685Notes

Reaction equation

HRID 1408685 reaction equation
[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)[CH2:18][CH2:17][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([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9][C:8]2=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10400CycloheptanoneHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 58424073HCID 58424073, compoundYield 126.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (10 g, 46.7 mmol), cycloheptanone (11 mL, 93.5 mmol) and pyrrolidine (7.7 mL, 93.5 mmol) in MeOH (190 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′-cycloheptan]-4-one (18.3 g, 100%). 1H-NMR (CDCl3): 1.34 (m, 1H), 1.49 (m, 1H), 1.62 (m, 10H), 1.71 (m, 1H), 2.02 (m, 1H), 6.78 (m, 1H), 7.47 (m, 1H), 7.86 (m, 1H).

Workup

  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

Sources & evidence

ORD record
ord-a39e2720b45b41cd81032073c8c18955
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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