Sodium borohydride → 2,2-diethyl-3,4-dihydro-4-hydroxy-2H-1-benzopyran-6-carbonitrile

HRID 704778Notes

Reaction equation

HRID 704778 reaction equation
[CH2:1]([C:3]1([CH2:16][CH3:17])[CH2:8][C:7](=[O:9])[C:6]2[CH:10]=[C:11]([C:14]#[N:15])[CH:12]=[CH:13][C:5]=2[O:4]1)[CH3:2].[BH4-].[Na+]>CO.O1CCCC1>[CH2:16]([C:3]1([CH2:1][CH3:2])[CH2:8][CH:7]([OH:9])[C:6]2[CH:10]=[C:11]([C:14]#[N:15])[CH:12]=[CH:13][C:5]=2[O:4]1)[CH3:17]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 143013512,2-diethyl-3,4-dihydro-4-oxo-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 147211782,2-diethyl-3,4-dihydro-4-hydroxy-2H-1-benzopyran-6-carbonitrileYield 101.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2-diethyl-3,4-dihydro-4-oxo-2H-1-benzopyran-6-carbonitrile (2.29 g) in a mixture of methanol (23 ml) and tetrahydrofuran (5 ml) was added sodium borohydride (0.37 g) at ambient temperature. The reaction mixture was stirred for an hour at the same temperature and evaporated in vacuo. The residue was dissolved in ethyl acetate, and then washed with water and brine successively. The extract was dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified with silica gel column chromatography using a mixture of methanol and methylene chloride (1:20) as an eluent to give 2,2-diethyl-3,4-dihydro-4-hydroxy-2H-1-benzopyran-6-carbonitrile (2.34 g).

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and brine successively
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified with silica gel column chromatography
  7. additiona mixture of methanol and methylene chloride (1:20) as an eluent

Sources & evidence

ORD record
ord-aca737a3399142b7bee611555c401195
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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