Sodium Hydroxide → ST51001684

HRID 2166473Notes

Reaction equation

HRID 2166473 reaction equation
C([CH:6]1[CH:11]([CH2:12][CH:13]([S:15][CH2:16][CH3:17])[CH3:14])[CH2:10][C:9](=[O:18])[CH2:8][C:7]1=[O:19])(OCC)=O.[OH-].[Na+]>CO>[CH2:16]([S:15][CH:13]([CH3:14])[CH2:12][CH:11]1[CH2:6][C:7](=[O:19])[CH2:8][C:9](=[O:18])[CH2:10]1)[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2834786HCID 2834786, compound

Product 1

HCID 3116068ST51001684Yield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester product of Example 1 (0.70 g, 2.4 mmole) was dissolved in 15 ml of methanol and 1 ml of 2N NaOH and heated to reflux for 21/2 hours. The mixture was maintained at room temperature overnight. Methanol was evaporated, and the residue partitioned between about 30 ml of toluene and about 30 ml of aqueous HCl. The toluene extract was dried over sodium sulfate and evaporated to give 0.35 g (66.8%) of product as a yellow solid which was identical with an authentic sample. This target product was further identified by NMR.

Workup

  1. temperatureto reflux for 21/2 hours
  2. customMethanol was evaporated
  3. customthe residue partitioned between about 30 ml of toluene and about 30 ml of aqueous HCl
  4. extractionThe toluene extract
  5. dry with materialwas dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-890255096db4480e94077fac6deb025a
Source dataset
uspto-grants-1990_07
Patent number
US04945178

Reaction notes

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