3-(benzyloxy)cyclopentanone → HCID 57767810, compound

HRID 237560Notes

Reaction equation

HRID 237560 reaction equation
[CH3:1][Mg]Br.[CH2:4]([O:11][CH:12]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O1CCCC1>[CH2:4]([O:11][CH:12]1[CH2:16][CH2:15][C:14]([CH3:1])([OH:17])[CH2:13]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 149370243-(benzyloxy)cyclopentanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 57767810HCID 57767810, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (4.8 mL, 1.4 M solution in toluene/tetrahydrofurane 3:1) is added dropwise under argon to a solution of 3-(benzyloxy)cyclopentanone (420 mg) in tetrahydrofurane (10 mL) at −78° C. The mixture is stirred for 12 hours while warming to room temperature and partitioned between 1 M aqueous HCl solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with brine and dried (MgSO4). The solvents are evaporated in vacuo to give the title compound. Yield: 400 mg; LC (method 7): tR=0.93 min; Mass spectrum (ESI+): m/z=229 [M+Na]+.

Workup

  1. custompartitioned between 1 M aqueous HCl solution and ethyl acetate
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvents are evaporated in vacuo

Sources & evidence

ORD record
ord-aa47684e9cf44aa3b7b99ca63e807282
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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