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

HRID 1699996Notes

Reaction equation

HRID 1699996 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e2f03e9a66d440549dad637716f2edf4
Source dataset
uspto-grants-2002_02
Patent number
US06348618B1

Reaction notes

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