Benzene → HCID 54356888, compound

HRID 1763911Notes

Reaction equation

HRID 1763911 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C@@H:15]([CH:16]=[CH:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[OH:25])[CH3:2].[C:27](Br)(=[O:29])[CH3:28].CS(O)(=O)=[O:33].[CH:36]1[CH:41]=CC=CC=1>>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C:15](=[CH:16][CH:17]=[C:18]([O:24][C:27](=[O:29])[CH3:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[O:25][C:41](=[O:33])[CH3:36])[CH3:2]

Participants

5

Reactant 4

HCID 241BenzeneHCID 6395Methanesulfonic AcidHCID 10482Acetyl bromideHCID 70616058HCID 70616058, compound

Product 1

HCID 54356888HCID 54356888, compound

Procedure

A mixture of 0.5 g. 9β-hydroxy-15-oxo-13-prostenoic acid ethyl ester, 4 ml. acetyl bromide, 10 ml. benzene and 0.2 g. methanesulfonic acid is heated under reflux for 4 hours, with the exclusion of moisture and poured, after cooling, into 80 ml. ice water. The resulting mixture is extracted twice with 40 ml. amounts of benzene. The organic phase is washed with water until neutral and dried over Na2SO4. Solvent is removed and, after chromatographic purification (silica gel/diisopropyl ether:petroleum ether:triethylamine = 100:100:1), 9β,15-diacetoxy-12,14-prostadienoic acid ethyl ester is obtained. UV: 243 - 244 nm (ε = 19800)

Workup

  1. additionA mixture of 0.5 g
  2. temperatureunder reflux for 4 hours, with the exclusion of moisture
  3. additionpoured
  4. temperatureafter cooling, into 80 ml
  5. extractionThe resulting mixture is extracted twice with 40 ml
  6. washThe organic phase is washed with water until neutral and
  7. dry with materialdried over Na2SO4
  8. customSolvent is removed
  9. customafter chromatographic purification (silica gel/diisopropyl ether:petroleum ether:triethylamine = 100:100:1)

Sources & evidence

ORD record
ord-087c56496ddf4a4f921b3258816734f5
Source dataset
uspto-grants-1978_09
Patent number
US04113863

Reaction notes

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