Sodium borohydride → HCID 20164680, compound

HRID 255844Notes

Reaction equation

HRID 255844 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:21][C:22]#[CH:23])[C:10]([OH:20])([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:11](=[O:13])[CH3:12].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:21][C:22]#[CH:23])[C:10]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)([OH:20])[CH:11]([OH:13])[CH3:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20164696HCID 20164696, compound

Product 1

HCID 20164680HCID 20164680, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.8 g of 4-(2,4-dichlorophenyl)-3-hydroxy-3-(3-pyridyl)-6-heptyn-2-one (see Example 4, 1st end product) in 100 ml of ethanol is treated at room temperature with 0.8 g of sodium borohydride and the mixture is stirred for 30 minutes. Thereafter, the excess sodium borohydride is destroyed by adjusting the yellowish reaction solution to pH 1 with 2N sulphuric acid and the mixture is again neutralized with saturated aqueous sodium bicarbonate solution. The mixture is evaporated under reduced pressure in order to remove the solvent, the residue is partitioned between ethyl acetate and water and the organic phase is washed with saturated aqueous sodium chloride solution and evaporated under reduced pressure in order to remove the solvent. The residue is purified by chromatography on silica gel with methylene chloride/ethyl acetate (3:7). In this manner there are obtained 5.7 g of 4-(2,4-dichlorophenyl)-3-(3-pyridyl)-6-heptyne-2,3-diol as a colorless solid foam. In an analogous manner, starting from

Workup

  1. customThereafter, the excess sodium borohydride is destroyed
  2. customThe mixture is evaporated under reduced pressure in order
  3. customto remove the solvent
  4. customthe residue is partitioned between ethyl acetate and water
  5. washthe organic phase is washed with saturated aqueous sodium chloride solution
  6. customevaporated under reduced pressure in order
  7. customto remove the solvent
  8. customThe residue is purified by chromatography on silica gel with methylene chloride/ethyl acetate (3:7)

Sources & evidence

ORD record
ord-5f1ece3f01554658befe8174943518ab
Source dataset
uspto-grants-1987_10
Patent number
US04699652

Reaction notes

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