Acetone → HCID 13088605, compound

HRID 2164705Notes

Reaction equation

HRID 2164705 reaction equation
B([O-])=O.[Na+].[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]([S:27][CH2:28][CH3:29])[CH:14]([N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)[C:15](=[O:21])[C:16]([CH3:20])([CH3:19])[CH2:17][F:18].[Cl-].[Ca+2].[Cl-].CC(C)=O>O.C(O)(C)C>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]([S:27][CH2:28][CH3:29])[CH:14]([N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)[CH:15]([OH:21])[C:16]([CH3:19])([CH3:20])[CH2:17][F:18]

Participants

7

Reactant 4

HCID 180AcetoneHCID 145326Sodium metaborateHCID 5284359Calcium ChlorideHCID 13088595HCID 13088595, compound

Product 1

HCID 13088605HCID 13088605, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.42 g (11 millimols) of sodium boranate in 20 ml of water was added dropwise, with stirring, to a suspension of 6.4 g (15.8 millimols) of 1-(2,4-dichlorophenyl)-4,4-dimethyl-1-ethylthio-5-fluoro-2-(1,2,4-triazol-1-yl)-pentan-3-one (see Example 5) and 1.2 g (10.8 millimols) of calcium chloride in 150 ml of isopropanol. The mixture was stirred for 18 hours at 0° C. and 20 ml of acetone were then added dropwise. This mixture was evaporated in vacuo and the residue was decomposed with dilute acetic acid. The organic base was dissolved in methylene chloride and the solution was washed with water, dried over sodium sulphate, filtered and evaporated down in vacuo. The oil which remained was stirred with diisopropyl ether. 3.9 g (60% of theory) of 1-(2,4-dichlorophenyl)-4,4-dimethyl-1-ethylthio-5-fluoro-2-(1,2,4-triazol-1-yl)-pentan-3-ol, of melting point 182° C., were obtained.

Workup

  1. customThis mixture was evaporated in vacuo
  2. dissolutionThe organic base was dissolved in methylene chloride
  3. washthe solution was washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated down in vacuo
  7. stirringThe oil which remained was stirred with diisopropyl ether

Sources & evidence

ORD record
ord-a84fa11749bd47dfa43473116ee801ff
Source dataset
uspto-grants-1985_03
Patent number
US04507141

Reaction notes

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