4-Nitrobenzyl alcohol → p-Nitrobenzyl 4-p-methoxybenzyloxycarbonyl-4-methylvalerate

HRID 1252217Notes

Reaction equation

HRID 1252217 reaction equation
[C:1]([C:4]([CH3:21])([CH3:20])[CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:8])([OH:3])=[O:2].CC1(C)CCC(=O)OC1=O.[N+](C1C=CC(CO)=CC=1)([O-])=O.[CH3:43][O:44][C:45]1[CH:52]=[CH:51][C:48]([CH2:49]Cl)=[CH:47][CH:46]=1>CN(C)C=O.O.C(N(CC)CC)C>[CH3:43][O:44][C:45]1[CH:52]=[CH:51][C:48]([CH2:49][O:2][C:1]([C:4]([CH3:21])([CH3:20])[CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[O:8])=[O:3])=[CH:47][CH:46]=1

Participants

8

Reactant 4

HCID 692754-Nitrobenzyl alcoholHCID 699934-Methyloxybenzyl chlorideHCID 76247Dihydro-3,3-dimethyl-2H-pyran-2,6(3H)-dioneHCID 20140795p-Nitrobenzyl 4-carboxy-4-methylvalerate

Product 1

HCID 20140840p-Nitrobenzyl 4-p-methoxybenzyloxycarbonyl-4-methylvalerate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of p-nitrobenzyl 4-carboxy-4-methylvalerate (17.26 g) in dry dimethylformamide (100 ml), prepared by the procedure similar to that described in Example 174 from 2,2-dimethylglutaric anhydride and p-nitrobenzyl alcohol, was added p-methoxybenzyl chloride (9.16 g) and triethylamine (5.91 g). The reaction mixture was stirred at 80° C. for 9.5 hours, diluted with water and extracted with diethyl ether. The extract was washed successively with aqueous potassium carbonate, water, dilute hydrochloric acid and again water, dried over anhydrous sodium sulfate and evaporated to give p-nitrobenzyl 4-p-methoxybenzyloxycarbonyl-4-methylvalerate.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed successively with aqueous potassium carbonate, water, dilute hydrochloric acid and again water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-2bae3c7b3497440ab93648332a424e42
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

Loading…