Potassium Hydroxide → HCID 69212468, compound

HRID 902915Notes

Reaction equation

HRID 902915 reaction equation
C([O:3][C:4](=[O:43])[CH:5]([CH2:22][S:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:6][CH:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])C.[OH-].[K+]>C(O)C>[C:18]([O:17][C:15](=[O:16])[CH:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH:5]([CH2:22][S:23][C:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:4]([OH:43])=[O:3])([CH3:20])([CH3:21])[CH3:19]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69209576HCID 69209576, compound

Product 1

HCID 69212468HCID 69212468, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of the ester of example 33 (2.1 g, 3.31 mmol) in ethanol (11 mL) was added 17.4 ml of a 10% aqueous solution of potassium hydroxide. The resulting mixture was stirred for 24 hours. After evaporation of the solvent, the obtained residue was taken-up into 50 ml of water and washed with diethyl ether (2×50 mL). The aqueous layer was then acidified to pH 3 with a 10% aqueous solution of hydrochloric acid at 0° C. and immediately extracted with ethyl acetate (5×50 ml). The organic extracts were combined, washed with water, and dried over anhydrous magnesium sulfate. Evaporation under vacuum gave the crude product which was purified by flash chromatography (SiO2, 70% hexane-30% ethyl acetate) to afford 880 mg of the desired compound: 1H NMR (CDCl3, 400 MHz) δ 7.31 (m, 15H), 3.04 (t, 1H), 2.95 (m, 1H), 2.25 (m, 2H), 1.85 (m, 1H), 1.44 (s, 18H); 13C NMR (CDCl3, 400 MHz) 173.9, 168.5, 144.9, 129.7, 128.3, 128.0, 82.0, 51.9, 43.3, 33.7, 30.5, 27.2.

Workup

  1. customAfter evaporation of the solvent
  2. washwashed with diethyl ether (2×50 mL)
  3. customwas then acidified to pH 3 with a 10% aqueous solution of hydrochloric acid at 0° C.
  4. extractionimmediately extracted with ethyl acetate (5×50 ml)
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customEvaporation under vacuum
  8. customgave the crude product which
  9. customwas purified by flash chromatography (SiO2, 70% hexane-30% ethyl acetate)

Sources & evidence

ORD record
ord-690004fe4f4f40d5b7a0b2bf94f30fb4
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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