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

HRID 1583500노트

반응식

HRID 1583500 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22f0b125d96e402bbd726fc425750388
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04552703

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