Benzyl Alcohol → HCID 18594626, compound

HRID 1580215Notes

Reaction equation

HRID 1580215 reaction equation
[C:1]([O:4][C@@H:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][C@@H:8]1[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:11](=[O:23])[CH2:10][CH2:9]1)(=[O:3])[CH3:2].[C:29]1([CH3:39])[C:30](S(O)(=O)=O)=[CH:31][CH:32]=[CH:33][CH:34]=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[C:1]([O:4][C@@H:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][C@@H:8]1[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:11]([O:47][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([O:23][CH2:39][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:10][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 69252-Methylbenzenesulfonic acidHCID 18594686HCID 18594686, compound

Product 1

HCID 18594626HCID 18594626, compound

Procedure

A solution of 2 g. of 1 methyl 15(S)-acetoxy-9-oxo prostanoate (Example 52) and 25 mg. of p toluene sulfonic acid in 65 ml. of benzylalcohol is stirred at 100°C. for 6 hours. The solution is concentrated to near dryness under reduced pressure. The residue is diluted with ether and the resulting solution is washed with 5% sodium carbonate solution, saturated sodium chloride solution, dried with anhydrous sodium sulfate and taken to dryness to afford 2.5 g. of product.

Workup

  1. concentrationThe solution is concentrated
  2. additionThe residue is diluted with ether
  3. washthe resulting solution is washed with 5% sodium carbonate solution, saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customto afford 2.5 g

Sources & evidence

ORD record
ord-96b3e947aed54b2b9e17fa5f6e640eca
Source dataset
uspto-grants-1976_01
Patent number
US03932463

Reaction notes

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