Sodium hydride → 2-[3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acryloyl]-malonic acid bis-(3,7-dimethyl-oct6-enyl) ester

HRID 325136Notes

Reaction equation

HRID 325136 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[CH:10]=[CH:11][C:12](C(C(O)=O)C(O)=O)=[O:13].[CH3:21][CH:22]([CH2:42][CH2:43][CH:44]=[C:45]([CH3:47])[CH3:46])[CH2:23][CH2:24][O:25][C:26](=[O:41])[CH2:27][C:28]([O:30][CH2:31][CH2:32][CH:33]([CH3:40])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:39])[CH3:38])=[O:29].CC1CCCC(C)(C)C=1C=CC(Cl)=O.[H-].[Na+]>>[CH3:21][CH:22]([CH2:42][CH2:43][CH:44]=[C:45]([CH3:47])[CH3:46])[CH2:23][CH2:24][O:25][C:26](=[O:41])[CH:27]([C:12](=[O:13])[CH:11]=[CH:10][C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])[C:28]([O:30][CH2:31][CH2:32][CH:33]([CH3:40])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:38])[CH3:39])=[O:29]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 54498946Malonic acid bis-(3,7-dimethyl-oct-6-enyl) esterHCID 545401113-(2,6,6-Trimethyl-cyclohex-1-enyl)acryloyl chlorideHCID 73432804HCID 73432804, compound

Product 1

HCID 701671522-[3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acryloyl]-malonic acid bis-(3,7-dimethyl-oct6-enyl) ester

Procedure

According to the procedure of Example 45, 2-[3-(2,6,6-trimethyl-cyclohex-1-enyl)-acryloyl]-malonic acid bis-3,7-dimethyl-oct-6-enyl) ester was prepared from malonic acid bis-(3,7-dimethyl-oct-6-enyl) ester, 3-(2,6,6-trimethyl-cyclohex-1-enyl)acryloyl chloride (Shimasaki et al., Chem. Pharm. Bull., 43 (1995) 1, 100-107) and sodium hydride.

Sources & evidence

ORD record
ord-e9be92e0d2704ef0b56f1ebdc8ff72df
Source dataset
uspto-grants-2001_04
Patent number
US06222062B1

Reaction notes

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