Potassium Carbonate → HCID 22005065, compound

HRID 324877Notes

Reaction equation

HRID 324877 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:9]([CH2:24][O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:8]([CH:43]([CH3:45])[CH3:44])[N:7]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O.C(OCC)(=O)C>[OH:4][CH2:5][C:6]1[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:9]([CH2:24][O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:8]([CH:43]([CH3:44])[CH3:45])[N:7]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 22005239HCID 22005239, compound

Product 1

HCID 22005065HCID 22005065, compoundYield 107%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the intermediate obtained in Step A (60 mg, 0.096 mmol) and potassium carbonate (5 equiv) in methanol (8 mL) and water (2 mL) was refluxed for 1.5 h. The mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. Concentration of the organic phase provided a colorless solid (60 mg, 100%) that was used in the next step without purification. 1H NMR (300 MHz, CDCl3): δ 7.4-7.2 (m, 10H), 7.11 (m, 4H), 4.90 (s, 2H), 4.39 (s, 2H), 3.34 (sept, 7.0 Hz, 1H), 2.34 (m, 2H), 1.25 (d, 7.0 Hz, 6H), 1.2 (m, 2H), 1.04 (m, 4H), 0.90 (s, 9H), 0.68 (t, 7.0 Hz, 3H).

Workup

  1. temperaturewas refluxed for 1.5 h
  2. washwashed with saturated aqueous sodium chloride solution

Sources & evidence

ORD record
ord-1b8cde90d7884cc2af28ea920807bd60
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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