Acetyl chloride → Methyl 7-[3-(acetyloxy)-5-oxocyclopent-1-en-1-yl]heptanoate

HRID 1032252Notes

Reaction equation

HRID 1032252 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1.[C:18](Cl)(=[O:20])[CH3:19].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:18]([O:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 3912664Norprostol

Product 1

HCID 14458235Methyl 7-[3-(acetyloxy)-5-oxocyclopent-1-en-1-yl]heptanoateYield 97.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Hydroxy-2-(6-methoxycarbonylhexyl)-2-cyclopentenone (24 g) was dissolved in chloroform (200 ml), followed by addition of acetyl chloride (7.9 g) thereto. Triethylamine [10.1 g) was dropwise added thereto while stirring at 0° to 10° C. After completion of the addition, stirring was continued at 25° C. for 8 hours. The reaction mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4-acetoxy-2-(6-methoxycarbonylhexyl)-2-cyclopentenone (27.6 g). Yield, 98%.

Workup

  1. additionAfter completion of the addition
  2. stirringstirring
  3. washThe reaction mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23e639a8704545dd92997ed51ce99289
Source dataset
uspto-grants-1990_09
Patent number
US04957867

Reaction notes

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