Sodium Hydroxide → 2,2-Difluoro-5-methoxy-1-pentanal oxime

HRID 568981Notes

Reaction equation

HRID 568981 reaction equation
O.[F:2][C:3]([F:11])([CH2:6][CH2:7][CH2:8][O:9][CH3:10])[CH:4]=O.[OH:12][NH:13]Cl.[OH-].[Na+].O1CCOCC1>[Cl-].[Na+].O.C(Cl)(Cl)(Cl)Cl.CCOCC>[F:2][C:3]([F:11])([CH2:6][CH2:7][CH2:8][O:9][CH3:10])[CH:4]=[N:13][OH:12]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 149953Hydroxylamine, N-chloro-HCID 201494532,2-Difluoro-5-methoxy-1-pentanal hydrate

Product 1

HCID 736640532,2-Difluoro-5-methoxy-1-pentanal oximeYield 91%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2,2-difluoro-5-methoxy-1-pentanal hydrate (1.57 g, 9.2 mmoles), hydroxylamino hydrochloride (640 mg, 9.2 mmoles), 1N NaOH (9.2 ml), and dioxane (15 ml) is kept for 1 hour at room temperature. After addition of ether and brine, usual extraction gives an oil which according to NMR is the oxime hydrate. Several evaporations with carbon tetrachloride (50° C., 60 mm Hg) afford the oxime (1.4 g) which is purified by chromatography on silica (ethyl acetate/petroleum ether: 20/80, RF: 0.53): 1.05 g (68%).

Workup

  1. customgives an oil which

Sources & evidence

ORD record
ord-cdffc9b431c346c79072bd402f130673
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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