Water → HCID 86704607, compound

HRID 1508538Notes

Reaction equation

HRID 1508538 reaction equation
I[CH:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][C:3]1=O.[CH3:17][O-:18].[Na+].[OH2:20]>C(OCC)C>[CH3:17][O:18][C:3]1[CH:2]=[CH:7][C:6]([C@H:8]2[CH2:9][CH2:10][C@H:12]([C:11]([O:14][CH3:15])=[O:20])[CH2:13]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 67513491HCID 67513491, compound

Product 1

HCID 86704607HCID 86704607, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0° C. solution of 2-iodo-4-(4-methoxyphenyl)cyclohexanone (Step A) (363 mg, 1.099 mmol) in diethyl ether (3 ml), under nitrogen, was added sodium methoxide (77 mg, 1.429 mmol) and the resulting mixture was stirred at RT for 30 minutes. Water was added and extracted 2 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the titled compound. 1H NMR (500 MHz, CDCl3): δ 7.15 (d, J=8.6 Hz, 1H); 6.84 (d, J=8.6 Hz, 1H); 3.79 (s, 3H); 3.70 (s, 3H); 3.17 (p, J=8.6 Hz, 1H); 3.06-2.91 (m, 1H); 2.34 (ddd, J=13.2, 8.1, 4.7 Hz, 1H); 2.19-2.06 (m, 2H); 2.03-1.80 (m, 2H); 1.70-1.58 (m, 1H).

Workup

  1. extractionextracted 2 times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-e2a301f21cea4dd9abdd9c154b18e757
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

Loading…