Sodium hydride → 2-[3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acryloyl]-malonic acid dihex-3-enyl ester

HRID 325135ノート

反応式

HRID 325135 の反応式
[H-].[Na+].[CH2:3]([O:9][C:10](=[O:21])[CH2:11][C:12]([O:14][CH2:15][CH2:16][CH:17]=[CH:18][CH2:19][CH3:20])=[O:13])[CH2:4][CH:5]=[CH:6][CH2:7][CH3:8].[CH3:22][C:23]1[CH2:28][CH2:27][CH2:26][C:25]([CH3:30])([CH3:29])[C:24]=1[CH:31]=[CH:32][C:33](Cl)=[O:34]>C1COCC1.CCOCC>[CH2:3]([O:9][C:10](=[O:21])[CH:11]([C:33](=[O:34])[CH:32]=[CH:31][C:24]1[C:25]([CH3:29])([CH3:30])[CH2:26][CH2:27][CH2:28][C:23]=1[CH3:22])[C:12]([O:14][CH2:15][CH2:16][CH:17]=[CH:18][CH2:19][CH3:20])=[O:13])[CH2:4][CH:5]=[CH:6][CH2:7][CH3:8]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 54313444Malonic acid dihex-3-enyl esterHCID 545401113-(2,6,6-Trimethyl-cyclohex-1-enyl)acryloyl chloride

生成物 1

HCID 701673212-[3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acryloyl]-malonic acid dihex-3-enyl ester収率 18.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a suspension of 2.10 g 60% sodium hydride in 20 ml of THF, a solution of 14.00 g malonic acid dihex-3-enyl ester in 20 ml of THF were dropped in at 0-5° C. The reaction mixture was stirred 1 hour at room temperature. Then a solution of 11.9 g 3-(2,6,6-trimethyl-cyclohex-1-enyl)-acryloyl chloride (Shimasaki et al., Chem. Pharm. Bull., 43 (1995) 1, 100-107) in 40 ml of THF was dropped in and the reaction mixture was stirred at room temperature for 21 hours. Then the reaction mixture was diluted with ether and the organic phase was washed with water, dried, filtered and evaporated to dryness. The resulting yellow oil was purified by chromatography to yield 4.22 g of a yellow oil.

後処理

  1. stirringwas stirred at room temperature for 21 hours
  2. washthe organic phase was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting yellow oil was purified by chromatography

出典と根拠

ORDレコード
ord-96d3800c973e4ad998d63d0bcdd64ab6
出典データセット
uspto-grants-2001_04
特許番号
US06222062B1

反応ノート

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