Chloral → 4-Hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone

HRID 1612990Notes

Reaction equation

HRID 1612990 reaction equation
C([O:4][CH:5]1[CH2:9][C:8](=[O:10])[C:7]([CH2:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:6]1)(=O)C.O=CC(Cl)(Cl)Cl.C(N(CC)CC)C.C(C(C)=O)C(C)C>O>[OH:4][CH:5]1[CH2:9][C:8](=[O:10])[C:7]([CH2:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:6]1

Participants

6

Reactant 4

HCID 6407ChloralHCID 7909Methyl Isobutyl KetoneHCID 8471TriethylamineHCID 110767524-Acetoxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone

Product 1

HCID 98595074-Hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenoneYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture (9.45 g) of the compound [IX-1] and the racemic 4-hydroxycyclopentenone obtained in Example 7, chloral (0.24 g) and triethylamine (0.43 g) is reacted at 60° C. for 5 hours. After completion of the reaction, to the mixture are added methyl isobutyl ketone (30 ml) and water (20 ml). The organic layer is separated and washed successively with 1% aqueous hydrochloric acid solution and water, and methyl isobutyl ketone is distilled off therefrom to give 4-hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone (racemic 4-hydroxycyclopentenone) (8.13 g, yield; 86%).

Workup

  1. customAfter completion of the reaction
  2. customThe organic layer is separated
  3. washwashed successively with 1% aqueous hydrochloric acid solution and water, and methyl isobutyl ketone
  4. distillationis distilled off

Sources & evidence

ORD record
ord-f5af086eaf0a487ab850a76ef43a1a29
Source dataset
uspto-grants-1993_03
Patent number
US05191109

Reaction notes

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