Sodium borohydride → HCID 86679085, compound

HRID 1039361Notes

Reaction equation

HRID 1039361 reaction equation
C[O:2][C:3](=O)[C:4](=[N:14][O:15][CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13].[BH4-].[Na+]>C(OCC)C.Cl>[CH3:16][O:15][N:14]=[C:4]([CH2:3][OH:2])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86679084HCID 86679084, compound

Product 1

HCID 86679085HCID 86679085, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-(2,4-dichloro-phenyl)-2-(methoxyimino)-propionic acid methyl ester (isomers E/Z) (0.25 g; 0.90 mmol) in diethyl ether (4.0 ml) under argon at 0° C., was added portionwise sodium borohydride (0.14 g; 3.6 mmol). The mixture was stirred for 2 hours at 0° C. and allowed to warm up at 20° C. for 16 h. The mixture was poured carefully in 2 N hydrochloric acid (6 ml) and extracted with ethyl acetate (3×5 ml). Combined organics were dried over sodium sulfate and evaporated under reduced pressure. The crude oil obtained was subject to flash chromatography (eluant: c-hexane/ethyl acetate 7:3) to afford 65 mg (30% of theory) of 1-(2,4-dichloro-phenyl)-3-hydroxy-propan-2-one O-methyl-oxime (mixture of E/Z-isomers) as a clear sticky oil.

Workup

  1. temperatureto warm up at 20° C. for 16 h
  2. extractionextracted with ethyl acetate (3×5 ml)
  3. dry with materialCombined organics were dried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe crude oil obtained

Sources & evidence

ORD record
ord-a60d439de18a421594705c9b31e522af
Source dataset
uspto-grants-2013_10
Patent number
US08552049B2

Reaction notes

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