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

HRID 65643Notes

Reaction equation

HRID 65643 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][C:11]([CH2:21][CH2:22][CH2:23][CH:24]([O:30]C(=O)C)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([S:17]([CH3:20])(=[O:19])=[O:18])C(OCC)=O)=[O:4].[Cl-].[Na+].C(=O)=O>CCOCC.O.CS(C)=O>[CH3:20][S:17]([CH:11]([CH2:21][CH2:22][CH2:23][CH:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:10][C:9]#[C:8][CH2:7][CH2:6][CH2:5][C:3]([OH:4])=[O:2])(=[O:18])=[O:19]

Participants

7

Reactant 3

HCID 280Carbon DioxideHCID 5234Sodium ChlorideHCID 20358246HCID 20358246, 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-(methylsulfonyl)-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-542ca5e3dfdf496daa193719263b12ae
Source dataset
uspto-grants-1978_12
Patent number
US04128564

Reaction notes

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