Sodium borohydride → HCID 20358230, compound

HRID 2083215Notes

Reaction equation

HRID 2083215 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13](=[O:19])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([CH:13]([OH:19])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20358244HCID 20358244, compound

Product 1

HCID 20358230HCID 20358230, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 20 g (0.062 mole) of 4-[5-(4-bromophenyl)-2-furanyl]-4-oxobutanoic acid in 350 ml of 95% dioxane/water was treated portionwise with 5.9 g (0.155 mole) of NaBH4 while maintaining the temperature at 15°-20° by means of an ice bath. The reaction was stirred at ambient temperature for 1 1/2 hrs and then filtered. The filtrate was added to ice/H2O and made acidic with 20% hydrochloric acid. The resulting solid was filtered, dissolved in ethyl acetate (Darco) and refiltered. The filtrate solid was filtered, dissolved in ethyl acetate (Darco) and refiltered. The filtrate was treated with hexane and the resulting solid filtered and air-dried to yield 8 g (40%).

Workup

  1. temperaturewhile maintaining the temperature at 15°-20° by means of an ice bath
  2. filtrationfiltered
  3. additionThe filtrate was added to ice/H2O
  4. filtrationThe resulting solid was filtered
  5. dissolutiondissolved in ethyl acetate (Darco)
  6. filtrationThe filtrate solid was filtered
  7. dissolutiondissolved in ethyl acetate (Darco)
  8. additionThe filtrate was treated with hexane
  9. filtrationthe resulting solid filtered
  10. customair-dried
  11. customto yield 8 g (40%)

Sources & evidence

ORD record
ord-e4b469db2c054339ac69040bc81756c8
Source dataset
uspto-grants-1978_04
Patent number
US04085118

Reaction notes

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