Water → HCID 22012246, compound

HRID 378548Notes

Reaction equation

HRID 378548 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][CH2:6][CH2:7][CH:8]1[C:12]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=2[O:10][CH2:9]1.CCOCC.O>CS(C)=O>[F:17][C:14]1[CH:15]=[CH:16][C:11]2[O:10][CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][C:1]#[N:2])[C:12]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 22012209HCID 22012209, compound

Product 1

HCID 22012246HCID 22012246, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
80 °C

Procedure

Sodium cyanide (12 g) was suspended in dimethyl sulfoxide (180 ml) and heated to 80° C. A solution of 3-(3-chloro-1-propyl)-2,3-dihydro-5-fluoro-benzofuran (42 g) in 40 ml of dimethyl sulfoxide was added dropwise followed by heating to 140° C. for 15 min. After cooling ether and water were added, the ether phase separated, washed with water and dried over magnesium sulfate. Removal of solvent in vacuo left a viscous oil which was applied to a silica gel column giving 4-(2,3-dihydro-5-fluoro-benzofuran-3-yl)butyronitrile as an oil (20 g).

Workup

  1. temperatureby heating to 140° C. for 15 min
  2. additionwere added
  3. customthe ether phase separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent in vacuo
  7. waitleft a viscous oil which

Sources & evidence

ORD record
ord-cfae6351b3974feda3da798a97f68342
Source dataset
uspto-grants-2000_02
Patent number
US06031099

Reaction notes

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