Sodium hydride → HCID 57210728, compound

HRID 2049726Notes

Reaction equation

HRID 2049726 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:7][CH:6]([O:8][C:9](=[O:26])[CH:10]([CH2:24][CH3:25])[C:11]([O:13][CH:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)=[O:12])[CH2:5][C:4]([CH3:28])([CH3:27])[NH:3]1.[H-].[Na+].[CH3:32][C:33]1[C:40]([OH:41])=[C:39]([C:42]([CH3:45])([CH3:44])[CH3:43])[CH:38]=[C:37]([CH3:46])[C:34]=1[CH2:35]Cl>CN(C)C=O>[CH3:21][C:18]1([CH3:20])[CH2:19][CH:14]([O:13][C:11](=[O:12])[C:10]([CH2:24][CH3:25])([CH2:35][C:34]2[C:37]([CH3:46])=[CH:38][C:39]([C:42]([CH3:45])([CH3:44])[CH3:43])=[C:40]([OH:41])[C:33]=2[CH3:32])[C:9]([O:8][CH:6]2[CH2:7][C:2]([CH3:1])([CH3:29])[NH:3][C:4]([CH3:28])([CH3:27])[CH2:5]2)=[O:26])[CH2:15][C:16]([CH3:23])([CH3:22])[NH:17]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 901316-tert-Butyl-3-(chloromethyl)-2,4-dimethylphenolHCID 20343470HCID 20343470, compound

Product 1

HCID 57210728HCID 57210728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 24.6 g (0.06 mole) of ethylmalonic acid-bis(2,2,6,6-tetramethyl-4-piperidinyl)ester in 80 ml of dimethylformamide there are added 2.5 g of NaH dispersion (55-60%) followed by 13.6 g (0.06 mole) of 2,6-di-methyl-4-tert. butyl-3-hydroxybenzyl chloride in 40 ml of DMF. The reaction mixture is stirred for 20 hours at 90°-100° C. and is then poured into ice-water; the aqueous solution is extracted with ether, the ethereal solution is dried over Na2SO4, and after removal of the solvent in vacuo there is obtained ethyl-(2,6-dimethyl-4-tert.butyl-3-hydroxybenzyl)malonic acid-bis (2,2,6,6-tetramethyl-4-piperidinyl)ester in the form of an oily yellowish residue (No. 43).

Workup

  1. extractionthe aqueous solution is extracted with ether
  2. dry with materialthe ethereal solution is dried over Na2SO4
  3. customafter removal of the solvent in vacuo

Sources & evidence

ORD record
ord-474b371791dc405da180764e33ce4261
Source dataset
uspto-grants-1980_04
Patent number
US04198334

Reaction notes

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