HCID 67714532, compound → HCID 56632723, compound

HRID 266030Notes

Reaction equation

HRID 266030 reaction equation
C([O:4][CH:5]([CH3:25])[CH2:6][C:7]1[CH:20]=[C:19]([CH3:21])[C:18]2[C:17](=[O:22])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:23])[C:9]=2[C:8]=1[CH3:24])(=O)C>C([O-])([O-])=O.[K+].[K+].CO>[CH3:24][C:8]1[C:9]2[C:10](=[O:23])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17](=[O:22])[C:18]=2[C:19]([CH3:21])=[CH:20][C:7]=1[CH2:6][CH:5]([OH:4])[CH3:25]

Participants

4

Reactant 1

HCID 67714532HCID 67714532, compound

Product 1

HCID 56632723HCID 56632723, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 11430Potassium CarbonateSolvent

Procedure

The acetoxy compound (Compound 1.2) (4 mg, 14 μmole) was dissolved in 4 mL of a solution of 5% K2CO3 and methanol (1 to 1 ratio). After 6 hours of stirring at room temperature, the reaction mixture was evaporated to half of the original volume for CHCl3 -H2O extraction. Then, the organic layer was dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. Purification by flash silica column chromatography yielded the hydroxy compound (Compound 1.3) in quantitative yield. 1H NMR (300 MHz, CDCl3) δ 8.04 (2H, m), 7.55 (2H, m), 7.31 (1H, s), 4.45 (1H, t), 3.42(2H, m), 2.95 (2H, t), 2.69 (6H, s), 1.64 (2H, m).

Workup

  1. customthe reaction mixture was evaporated to half of the original volume for CHCl3 -H2O extraction
  2. dry with materialThen, the organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification by flash silica column chromatography

Sources & evidence

ORD record
ord-aa50cf55fd6d494e82302664f418f13c
Source dataset
uspto-grants-1997_07
Patent number
US05650399

Reaction notes

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