Sodium Hydroxide → HCID 58516415, compound

HRID 2390560Notes

Reaction equation

HRID 2390560 reaction equation
[CH3:1][O:2][N:3]=[C:4]([CH3:14])[CH2:5][C:6]1[C:10]([Cl:11])=[C:9]([Cl:12])[S:8][C:7]=1[Cl:13].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][O:2][NH:3][CH:4]([CH3:14])[CH2:5][C:6]1[C:10]([Cl:11])=[C:9]([Cl:12])[S:8][C:7]=1[Cl:13]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 76809388HCID 76809388, compound

Product 1

HCID 58516415HCID 58516415, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

In a sulfonation flask 299 mg (1.1 mmol) 1-(2,4,5-trichlorothiophene-3-yl)propan-2-one O-methyl oxime were dissolved in 3.5 ml acetic acid and the resulting mixture was cooled to a temperature of 15° C. Then 138 mg (2.2 mmol) sodiumcyanoborohydride was added and the reaction mixture was stirred for 7 hours at ambient temperature. The mixture was then carefully diluted with 20 ml of water and the pH was adjusted to ca.10 by slowly adding 16 ml of 4N sodiumhydroxide solution. The mixture was extracted 3 times with ethylacetate and the combined organic phase was washed 2 times with water. After drying and evaporation of the solvent, the residue was purified by column chromatography (eluent: ethylacetate/heptane 1:9). Yield: 304 mg (100% of theory) of a colourless liquid (NMR-data see table 9).

Workup

  1. extractionThe mixture was extracted 3 times with ethylacetate
  2. washthe combined organic phase was washed 2 times with water
  3. customAfter drying
  4. customevaporation of the solvent
  5. customthe residue was purified by column chromatography (eluent: ethylacetate/heptane 1:9)

Sources & evidence

ORD record
ord-9ac9758b50cf4cb2bf3b7f9ad8bbc910
Source dataset
uspto-grants-2012_09
Patent number
US08273783B2

Reaction notes

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