Potassium Carbonate → 241151-12-2

HRID 2304847Notes

Reaction equation

HRID 2304847 reaction equation
C([O:4][C@@H:5]1[CH2:10][C:9](=[CH:11]/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][C:17]([CH3:39])([CH3:38])[CH2:18]/[CH:19]=[CH:20]\[C:21]([O:30][Si](CC)(CC)CC)([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])[CH2:8][C@@H:7]([O:40]C(=O)C)[CH2:6]1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[F:23][C:22]([F:24])([F:25])[C:21]([OH:30])([C:26]([F:28])([F:29])[F:27])/[CH:20]=[CH:19]\[CH2:18][C:17]([CH3:39])([CH3:38])[CH2:16][CH2:15][CH2:14]/[CH:13]=[CH:12]/[CH:11]=[C:9]1[CH2:10][C@@H:5]([OH:4])[CH2:6][C@H:7]([OH:40])[CH2:8]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 15488936HCID 15488936, compound

Product 1

HCID 9911311241151-12-2

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 50 mg of acetic acid (1R,3R)-3-acetoxy-5-[(2E,9Z)-12,12,12-trifluoro-7,7-dimethyl-11-triethylsilanyloxy-11-trifluoromethyl-dodeca-2,9-dienylidene]-cyclohexyl ester in 1.5 ml of CH3OH was added at 22° a solution of 37 mg of K2CO3 in 0.25 ml of water and stirring was continued for 8 h after which time t.l.c. indicated completion of the reaction. The mixture was evaporated and the residue was partitioned between dichloromethane and aqueous sat. NaCl, the organic layer was dried over MgSO4 and evaporated. The residue was chromatographed on silica with hexane/AcOEt 2:1 to give 34 mg of the pure (t.l.c.) title compound as a colorless resin. IR (neat): 3345s (OH), 1661w and 1622w (C═C); MS (EI): 444/10 (M), 426/8 (M−H2O).

Workup

  1. customcompletion of the reaction
  2. customThe mixture was evaporated
  3. customthe residue was partitioned between dichloromethane and aqueous sat. NaCl
  4. dry with materialthe organic layer was dried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed on silica with hexane/AcOEt 2:1

Sources & evidence

ORD record
ord-e46926ed9d374dc790b5b1792b2db45d
Source dataset
uspto-grants-2002_08
Patent number
US06437142B1

Reaction notes

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