1-Chloropentane → HCID 20513412, compound

HRID 1164095Notes

Reaction equation

HRID 1164095 reaction equation
[C:1]([CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C:10]=1[O:23][CH3:24])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[H-].[Na+].[CH2:27](Cl)[CH2:28][CH2:29][CH2:30][CH3:31]>CN(C)C=O>[C:1]([C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C:10]=1[O:23][CH3:24])([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 109771-ChloropentaneHCID 24758Sodium hydrideHCID 20513460HCID 20513460, compound

Product 1

HCID 20513412HCID 20513412, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethyl 2-cyano-2-[2-methoxy-3-(o-tolyloxy)phenyl]acetate (5 g) in dimethylformamide (10 ml) was added dropwise to a suspension of sodium hydride (65%, 600 mg) in dimethylformamide (30 ml) in 10 minutes at temperature below 10° C. with stirring, and the mixture was stirred at the same temperature for 10 minutes. n-Pentyl chloride (3.3 g) was added to the mixture and stirred at 110° C. for 2 hours. The reaction mixture was treated in a similar manner to that of Example 25-(1) to give oily ethyl 2-cyano-2-[2-methoxy-3-(o-tolyloxy)phenyl]-n-heptanoate (5.9 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 10 minutes
  2. stirringstirred at 110° C. for 2 hours
  3. additionThe reaction mixture was treated in a similar manner to that of Example 25-(1)

Sources & evidence

ORD record
ord-e4199b8eb5564bb79f0a1e288f11e01f
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

Loading…