Water → HCID 66652045, compound

HRID 418902Notes

Reaction equation

HRID 418902 reaction equation
C(O[C:4](=[O:19])[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)C.O>C(Cl)Cl>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16]([C:4](=[O:19])[CH2:5][CH:6]3[CH2:10][CH2:9][CH2:8][CH:7]32)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 962WaterHCID 66652047HCID 66652047, compound

Product 1

HCID 66652045HCID 66652045, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Heat a solution of [2-(3-methoxyphenyl)-cyclopentyl]-acetic acid ethyl ester (4.2 g, 16.0 mmoles) in polyphosphoric acid (27 g) at 100° C. for 3.5 hours. Cool the reaction to r.t. and add ice, water and methylene chloride cautiously. Extract the aqueous layer was 2× with additional methylene chloride, combine the organic layers and dry over anhydrous sodium sulfate. Concentrate in vacuo at 40° C. Chromatograph the crude product on silica with 11-17% ethyl acetate/hexanes to yield the titled compound (2.8 g, 81%) as a neat crystalline solid. 1H NMR (CDCl3): 7.95 (d, J=8.8 Hz, 1H), 6.8 (dd, J=2.8 Hz, 6.4 Hz, 1H), 6.73(m, 1H), 3.86 (s, 3H), 3.19 (m, 1H), 2.72 (m, 1H), 2.53 (m, 2H), 2.18 (m, 1H), 2.0-1.75 (m, 5H).

Workup

  1. temperatureCool
  2. customthe reaction to r.t.
  3. extractionExtract the aqueous layer
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationConcentrate in vacuo at 40° C

Sources & evidence

ORD record
ord-3ba293be99b34a669e6566e35192d223
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

Loading…