Dimethylformamide → 1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

HRID 2056751Notes

Reaction equation

HRID 2056751 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:14]=1.[CH3:15][N:16](C=O)C>C1(C)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:13][CH2:12][CH2:11][CH:10]1[C:5]2[CH:4]=[CH:3][C:2]([C:15]#[N:16])=[CH:14][C:6]=2[CH2:7][CH2:8][O:9]1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 232888302-(6-Bromoisochroman-1-yl)ethanol

Product 1

HCID 236356931-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

2-(6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (1.3 g, 5.1 mmol), zinc cyanide (0.36 g, 3 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.23 g, 0.20 mmol) were stirred in degassed DMF (20 mL) under nitrogen at reflux for 9 h. The reaction mixture was diluted with toluene and washed with 2M aqueous ammonia, the aqueous layer further extracted with ethyl acetate, then the combined organic extracts washed with brine. The organic extracts were dried (MgSO4), filtered and evaporated in vacuo. Purification by flash chromatography on silica, eluting with ethyl acetate/hexane (30:70 to 0:100), yielded the title compound as a light brown oil.

Workup

  1. temperatureat reflux for 9 h
  2. washwashed with 2M aqueous ammonia
  3. extractionthe aqueous layer further extracted with ethyl acetate
  4. washthe combined organic extracts washed with brine
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurification by flash chromatography on silica
  9. washeluting with ethyl acetate/hexane (30:70 to 0:100)

Sources & evidence

ORD record
ord-d64321dbd07445369983bdb99ac1efe6
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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