Sodium borohydride → HCID 21553303, compound

HRID 268093Notes

Reaction equation

HRID 268093 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15]#[N:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>O1CCOCC1.O>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][C:13]([C:15]#[N:16])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 215533215-(4-Acetylphenyl)furan-2-carbonitrile

Product 1

HCID 21553303HCID 21553303, compoundYield 58%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 46 g (0.22 mole) of 5-(4-acetylphenyl)-2-furonitrile in 800 ml of 95% dioxane/H2O was treated portionwise with 8.3 g (0.22 mole) of NaBH4 while keeping the temperature below 20° by means of an ice bath. The resulting solution was stirred at ambient temperature for 21/2 hours and then added to an ice/H2O mixture. After standing 48 hours, the reaction mixture was extracted with ether and the combined ethereal extracts dried over MgSO4. The ether was removed on the Calab evaporator yielding 27 g (58%) of product as a residual oil.

Workup

  1. customthe temperature below 20°
  2. waitAfter standing 48 hours
  3. extractionthe reaction mixture was extracted with ether
  4. dry with materialthe combined ethereal extracts dried over MgSO4
  5. customThe ether was removed on the Calab evaporator

Sources & evidence

ORD record
ord-1e4ddf3d09834c9ba1ffe986b44a8551
Source dataset
uspto-grants-1976_03
Patent number
US03946049

Reaction notes

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