Water → HCID 14748274, compound

HRID 1165254Notes

Reaction equation

HRID 1165254 reaction equation
C([S:4][CH:5]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=1)[CH2:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[SH:4][CH:5]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=1)[CH2:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 14748273HCID 14748273, compound

Product 1

HCID 14748274HCID 14748274, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.73 g of methyl 8-(acetylthio)-9-(4-pentylphenoxy)-5-nonynoate, the product of Example 12a, 1.25 g of potassium carbonate, 0.6 ml of H2O and 32 ml of MeOH was stirred at RT for 12 hr. MeOH was removed and the residue was acidified with 3N HCL and extracted with Et2O to obtain the crude product. The crude product was purified by silical gel chromatography (CH2Cl2 -MeOH) and then recrystallized in petroleum ether-Et2O to obtain the title compound, mp 70.0-70.5.

Workup

  1. customMeOH was removed
  2. extractionextracted with Et2O
  3. customto obtain the crude product
  4. customThe crude product was purified by silical gel chromatography (CH2Cl2 -MeOH)
  5. customrecrystallized in petroleum ether-Et2O

Sources & evidence

ORD record
ord-666efa5796544776a5f884c6a91dcc8d
Source dataset
uspto-grants-1990_03
Patent number
US04908384

Reaction notes

Loading…