Water → HCID 22012246, compound
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
3-(2,3-Dihydro-5-fluoro-benzofuran-3-yl)-1-propanol, prepared as described in EXAMPLE 11, (51 g) was dissolved in 300 ml of dichloromethane and 0.5 ml of dimethyl formamide was added. During 20 min 50 ml of thionyl chloride was added dropwise followed by stirring for 3 h. Ice cold water was added, the organic phase separated, dried over magnesium sulfate and concentrated in vacuo giving 46 g of 3-(3-chloro-1-propyl)-2,3-dihydro-5-fluoro-benzofuran as an oil. 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
- temperatureby heating to 140° C. for 15 min
- additionwere added
- customthe ether phase separated
- washwashed with water
- dry with materialdried over magnesium sulfate
- customRemoval of solvent in vacuo
- waitleft a viscous oil which
Sources & evidence
- ORD record
- ord-f6a72c6dde4f415788e7cdc06f1dfd6d
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06207677B1
Reaction notes
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