Diethyl Ether → Heptanoic acid, 6-oxo-, methyl ester

HRID 379211

Reaction equation

HRID 379211 reaction equation
[CH2:1](OCC)C.[OH-].[K+].CN(N=O)/C(/N)=N/[N+]([O-])=O.[O:18]=[C:19]([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25]>C(Cl)Cl>[CH3:1][O:25][C:24](=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20][C:19](=[O:18])[CH3:27]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 988106-Oxoheptanoic acidHCID 95620601-Methyl-2-nitro-1-nitrosoguanidine

Product 1

HCID 288022Heptanoic acid, 6-oxo-, methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a rapidly stirred mixture of diethyl ether (175 ml) and 40% KOH (52 ml) at 0° C. was added MNNG (15.4 g, 105 mmol). The mixture was stirred for 10 minutes. The ethereal layer was transferred to a solution of 6-oxo-heptanoic acid 1-1 (5.0 g, 34.68 mmol) and CH2Cl2 at 0° C. The solution was purged with argon for 30 minutes and then concentrated. Flash chromatography (silica, 30% to 50% EtOAc/hexanes) gave ester 1-2 as a clear oil.

Workup

  1. customThe solution was purged with argon for 30 minutes
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-db2cf0e36f7b48698ce9156fd0af1ec5
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Linked notes

Loading…