Calcium Carbonate → 4-Hydroxy-3-methyl-2-(prop-2-yn-1-yl)cyclopent-2-en-1-one

HRID 1583500Notes

Reaction equation

HRID 1583500 reaction equation
[CH3:1][C:2]1[C@H:6]([O:7][N+]([O-])=O)[CH2:5][C:4](=[O:11])[C:3]=1[CH2:12][C:13]#[CH:14].C(=O)([O-])[O-].[Ca+2]>O>[OH:7][C@H:6]1[CH2:5][C:4](=[O:11])[C:3]([CH2:12][C:13]#[CH:14])=[C:2]1[CH3:1]

Participants

4

Reactant 2

HCID 10112Calcium CarbonateHCID 13387529(R)-3-methyl-4-nitroxy-2-(2-propynyl)-2-cyclopenten-1-one

Product 1

HCID 1569974-Hydroxy-3-methyl-2-(prop-2-yn-1-yl)cyclopent-2-en-1-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.95 g of crude (R)-3-methyl-4-nitroxy-2-(2-propynyl)-2-cyclopenten-1-one prepared in Example 1, 1.00 g of calcium carbonate and 30 ml of water was stirred at a temperature of 80°-85° C. for 5 hours. Then the reaction mixture was cooled and filtered through celite. Thereafter, the water layer was saturated with sodium chloride and extracted with methyl isobutyl ketone. The organic layer was separated, washed with an aqueous saturated sodium chloride solution dried over anhydrous magnesium sulfate and, then, concentrated. Thus, 1.28 g of (S)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one (chemical purity: 90.1%, [α]D23 : +15.0° (C=1.06, in chloroform), (R)-isomer/(S)-isomer=11.6/88.4) was obtained.

Workup

  1. temperatureThen the reaction mixture was cooled
  2. filtrationfiltered through celite
  3. extractionextracted with methyl isobutyl ketone
  4. customThe organic layer was separated
  5. washwashed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22f0b125d96e402bbd726fc425750388
Source dataset
uspto-grants-1985_11
Patent number
US04552703

Reaction notes

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