Sodium borohydride → 1-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-ol

HRID 851623Notes

Reaction equation

HRID 851623 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([C:10](=[O:25])[CH:11]([N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][O:8][CH2:7][O:6][CH2:5]1>CO>[CH3:3][C:4]1([CH:10]([OH:25])[CH:11]([N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:5][O:6][CH2:7][O:8][CH2:9]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 128556531-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-one

Product 1

HCID 128556541-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-olYield 49.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

11.5 g (0.3 mole) of sodium borohydride are added, a little at a time, to a solution of 90 g (0.269 mole) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-one in 250 ml of methanol, at from 0° to +5° C. The mixture is stirred for 12 hours at 20° C. and is then evaporated down. The residue is stirred for 1 hour with 200 ml of 20% strength potassium hydroxide solution and the mixture is then extracted with 500 ml of methylene chloride. The organic phase is washed with three times 50 ml of water, dried over sodium sulfate and evaporated down. The residue crystallizes at +5° C. after addition of 20 ml of ether. 45 g (49.6%) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-ol are isolated as white crystals of melting point 152°-154° C.

Workup

  1. customat from 0° to +5° C
  2. customis then evaporated down
  3. stirringThe residue is stirred for 1 hour with 200 ml of 20% strength potassium hydroxide solution
  4. extractionthe mixture is then extracted with 500 ml of methylene chloride
  5. washThe organic phase is washed with three times 50 ml of water
  6. dry with materialdried over sodium sulfate
  7. customevaporated down
  8. customThe residue crystallizes at +5° C.
  9. additionafter addition of 20 ml of ether

Sources & evidence

ORD record
ord-d94725620c604000b97b3071a2f10b4f
Source dataset
uspto-grants-1983_05
Patent number
US04385925

Reaction notes

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