Ethylene Glycol → HCID 68118985, compound

HRID 973096Notes

Reaction equation

HRID 973096 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14]([CH:15]=[CH:16][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12][C:11]1=[O:24].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:37](O)[CH2:38][OH:39]>CCOCC>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14]([CH:15]=[CH:16][CH:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH:12]2[O:39][CH2:38][CH2:37][O:24][CH:11]12

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 57189079HCID 57189079, compound

Product 1

HCID 68118985HCID 68118985, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture if 9,15-dioxoprost-13-enoic acid methyl ester (2.0 g) benzene (50 ml), p-toluenesulfonic acid (37 mg) and ethylene glycol (372 mg) is refluxed for 2.5 hours, diluted with ether, washed neutral with water, dried over magnesium sulfate, and evaporated under reduced pressure. The residue containing 9-ethylenedioxy-15-oxoprost-13-enoic acid methyl ester is taken up in methanol (20 ml) and treated with sodium borohydride (300 mg) in small portions with stirring which is continued for 30 minutes. The solvent is evaporated under reduced pressure, the residue taken up in ether, washed to neutrality with water, dried over magnesium sulfate, and the solvent evaporated under reduced pressure. The residue is chromatographed on silica gel (140 g) and eluted with 40% ether in hexane to yield 9-ethylenedioxy-15-hydroxyprost-13-enoic acid methyl ester, γmaxFilm 3460, 1740, 1037, 975, 950 cm-1.

Workup

  1. washwashed neutral with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. additionThe residue containing 9-ethylenedioxy-15-oxoprost-13-enoic acid methyl ester
  5. additiontreated with sodium borohydride (300 mg) in small portions
  6. customThe solvent is evaporated under reduced pressure
  7. washwashed
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent evaporated under reduced pressure
  10. customThe residue is chromatographed on silica gel (140 g)
  11. washeluted with 40% ether in hexane

Sources & evidence

ORD record
ord-b2978532e71f4b37ba3d23ac451a6d68
Source dataset
uspto-grants-1977_10
Patent number
US04054741

Reaction notes

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