Sodium borohydride → HCID 14685621, compound

HRID 1380054Notes

Reaction equation

HRID 1380054 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])[N:3]=1.[BH4-].[Na+]>CC(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:11][OH:12])[CH:13]=[CH:14][CH:15]=2)[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 135903783-(4-Chloro-2-pyrimidinyl)benzaldehyde

Product 1

HCID 14685621HCID 14685621, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 1.0 g portion of 3-(4-chloro-2-pyrimidinyl)benzaldehyde was dissolved in 230 ml of 2-propanol and 0.32 g of freshly ground sodium borohydride pellets was added. After stirring for 3 hours at 50°-60° C. in a water bath, the excess reducing agent was destroyed with 6N hydrochloric acid. The solution was neutralized with sodium bicarbonate and the mixture concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and then evaporated, giving 1.1 g of the desired intermediate as a colorless oil.

Workup

  1. customwas destroyed with 6N hydrochloric acid
  2. concentrationthe mixture concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d725d9425e744f0d9357d97130488c10
Source dataset
uspto-grants-1986_04
Patent number
US04579848

Reaction notes

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