Lithium amide → HCID 20306454, compound

HRID 1732426Notes

Reaction equation

HRID 1732426 reaction equation
[CH3:1][C:2]1([CH3:35])[N:7]([CH2:8][CH2:9][OH:10])[C:6]([CH3:12])([CH3:11])[CH2:5][C:4]2([O:34][CH2:33][C:15]3([CH2:32][O:31][C:18]4([CH2:23][C:22]([CH3:25])([CH3:24])[N:21]([CH2:26]CO)[C:20]([CH3:30])([CH3:29])[CH2:19]4)[O:17][CH2:16]3)[CH2:14][O:13]2)[CH2:3]1.[C:36]([C:40]1[CH:41]=[C:42]([CH2:51][CH2:52][C:53]([O:55][CH3:56])=[O:54])[CH:43]=[C:44]([C:47]([CH3:50])([CH3:49])[CH3:48])[C:45]=1[OH:46])([CH3:39])([CH3:38])[CH3:37].[NH2-].[Li+]>C1(C)C=CC=CC=1>[CH3:24][C:22]1([CH3:25])[N:21]([CH2:26][CH2:56][O:55][C:53](=[O:54])[CH2:52][CH2:51][C:42]2[CH:43]=[C:44]([C:47]([CH3:48])([CH3:49])[CH3:50])[C:45]([OH:46])=[C:40]([C:36]([CH3:37])([CH3:38])[CH3:39])[CH:41]=2)[C:20]([CH3:29])([CH3:30])[CH2:19][C:18]2([O:17][CH2:16][C:15]3([CH2:14][O:13][C:4]4([CH2:5][C:6]([CH3:11])([CH3:12])[N:7]([CH2:8][CH2:9][O:10][C:53](=[O:54])[CH2:52][CH2:51][C:42]5[CH:43]=[C:44]([C:47]([CH3:48])([CH3:50])[CH3:49])[C:45]([OH:46])=[C:40]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:41]=5)[C:2]([CH3:1])([CH3:35])[CH2:3]4)[O:34][CH2:33]3)[CH2:32][O:31]2)[CH2:23]1

Participants

5

Reactant 3

HCID 24532Lithium amideHCID 62603Methyl di-t-butyl hydroxyhydrocinnamateHCID 20306452HCID 20306452, compound

Product 1

HCID 20306454HCID 20306454, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 20 g of 2,2,4,4,14,14,16,16-octamethyl-3,15-bis(2-hydroxyethyl)-7,11,18,21-tetraoxa-3,15-diazatrispiro[5.2.2.5.2.2]heneicosane, 26 g of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 2 g of lithium amide was refluxed for 8 hours in 400 ml of toluene under argon stream. Following the procedures in Example 1, the residue was purified first by column chromatography through silica gel with a 9:1 by volume mixture of benzene and ethyl acetate, then by recrystallization from a 4:1 by volume mixture of n-hexane and benzene, giving the desired compound in the form of pale yellow crystals melting at 176°-178° C.

Workup

  1. customthe residue was purified first by column chromatography through silica gel with a 9:1 by volume mixture of benzene and ethyl acetate
  2. customby recrystallization from a 4:1
  3. additionby volume mixture of n-hexane and benzene

Sources & evidence

ORD record
ord-f732e064faa742418157a652357ed163
Source dataset
uspto-grants-1980_12
Patent number
US04237294

Reaction notes

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