Carbon Dioxide → 8-Methylsulfonyl-12-hydroxy-5-heptadecynoic acid

HRID 263005Notes

Reaction equation

HRID 263005 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][C:11]([CH2:22][CH2:23][CH2:24][CH:25]([O:31]C(=O)C)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([S:17](OC)(=[O:19])=[O:18])C(OCC)=O)=[O:4].[Cl-].[Na+].[C:37](=O)=O>CCOCC.O.CS(C)=O>[CH3:37][S:17]([CH:11]([CH2:22][CH2:23][CH2:24][CH:25]([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:10][C:9]#[C:8][CH2:7][CH2:6][CH2:5][C:3]([OH:2])=[O:4])(=[O:19])=[O:18]

Participants

7

Reactant 3

HCID 280Carbon DioxideHCID 5234Sodium ChlorideHCID 53799130HCID 53799130, compound

Product 1

HCID 213176278-Methylsulfonyl-12-hydroxy-5-heptadecynoic acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of ethyl 2-(6-methoxycarbonyl-2-hexyn-1-yl)-2-(4-acetoxynonyl)-2-(methoxysulfonyl)-acetate (48.8 g., 0.1 mole), water (3.6 g., 0.2 mole), and sodium chloride (6.5 g., 0.11 mole) in 120 ml. of dimethyl sulfoxide is heated at 130°-150° C. for 6 hours until evolution of carbon dioxide is completed. The mixture is cooled, treated with 400 ml. of water and the oily product taken up in ether, washed with water and dried over sodium sulfate. Evaporation of the ether in vacuo leaves the title compound as a yellow viscous oil.

Workup

  1. temperatureThe mixture is cooled
  2. additiontreated with 400 ml
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the ether in vacuo

Sources & evidence

ORD record
ord-d0e196a6f6984b4fa7746c2c07043a68
Source dataset
uspto-grants-1979_05
Patent number
US04155908

Reaction notes

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