Potassium Carbonate → Methyl 2-(1-(4-bromophenyl)cyclopentyloxy)acetate

HRID 1397492Notes

Reaction equation

HRID 1397492 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:18](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 687203352-(1-(4-Bromophenyl)cyclopentyloxy)acetic acid

Product 1

HCID 68721066Methyl 2-(1-(4-bromophenyl)cyclopentyloxy)acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ambient solution of Example 30B (200 mg, 0.668 mmol) in N,N-dimethylformamide (4 mL) was added iodomethahe (0.208 mL. 3.34 mmol) and potassium carbonate (184 mg, 1.34 mmol). The mixture was stirred at room temperature for 40 h, and then diluted with water (10 mL) and ethyl acetate (20 mL). The layers were separated, and the organic was washed with water (3×10 mL), brine (1×10 mL), dried over sodium sulfate, and concentrated under reduced pressure to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.67-1.72 (m, 2 H), 1.74-1.84 (m, 4 H), 2.10 (m, 2 H), 3.58 (s, 3 H), 3.67-3.70 (m, 2 H), 7.34-7.40 (m, 2 H), 7.51-7.57 (m, 2 H).

Workup

  1. customThe layers were separated
  2. washthe organic was washed with water (3×10 mL), brine (1×10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63044044ee2e4ab4bde18ef60db7e725
Source dataset
uspto-grants-2014_12
Patent number
US08901152B2

Reaction notes

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