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

HRID 1583500ノート

反応式

HRID 1583500 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-22f0b125d96e402bbd726fc425750388
出典データセット
uspto-grants-1985_11
特許番号
US04552703

反応ノート

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