HCID 69183674, compound → HCID 56963529, compound

HRID 511746Notes

Reaction equation

HRID 511746 reaction equation
CC(C)(C)C([O:5][C:6]1[CH:13]2[CH:9]([CH2:10][CH:11]([CH:14]3[O:19][CH2:18][CH2:17][CH2:16][O:15]3)[CH2:12]2)[C:8](=[O:20])[C:7]=1[C:21]1[C:26]([CH2:27][CH3:28])=[CH:25][C:24]([CH3:29])=[CH:23][C:22]=1[CH2:30][CH3:31])=O>CO.[OH-].[Na+]>[CH2:30]([C:22]1[CH:23]=[C:24]([CH3:29])[CH:25]=[C:26]([CH2:27][CH3:28])[C:21]=1[CH:7]1[C:6](=[O:5])[CH:13]2[CH:9]([CH2:10][CH:11]([CH:14]3[O:19][CH2:18][CH2:17][CH2:16][O:15]3)[CH2:12]2)[C:8]1=[O:20])[CH3:31]

Participants

4

Reactant 1

HCID 69183674HCID 69183674, compound

Product 1

HCID 56963529HCID 56963529, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.100 g (0.22 mmol) of 2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxan-2-yl)-3-oxo-3,3a,4,5,6,6a-hexahydropentalen-1-yl 2,2-dimethylpropanoate in 10 ml of methanol and 4 ml of 1N aqueous sodium hydroxide solution is stirred at room temperature for 2 h. The mixture is then concentrated, the residue is taken up in water, the mixture is acidified to pH 4 using 2N HCl and extracted with ethyl acetate, the extract is dried (magnesium sulphate) and the solvent is distilled off. Chromatographic purification of the residue on silica gel (mobile phase ethyl acetate/hexane 1:6) gives 70 mg (86%) of the desired compound in the form of colourless needles of m.p. 100-101° C.

Workup

  1. concentrationThe mixture is then concentrated
  2. extractionextracted with ethyl acetate
  3. dry with materialthe extract is dried (magnesium sulphate)
  4. distillationthe solvent is distilled off
  5. customChromatographic purification of the residue on silica gel (mobile phase ethyl acetate/hexane 1:6)

Sources & evidence

ORD record
ord-c7ab9430ac4344f08daef7c526d63cea
Source dataset
uspto-grants-2015_08
Patent number
US09101133B2

Reaction notes

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