Dimethylformamide → HCID 66803442, compound

HRID 341530Notes

Reaction equation

HRID 341530 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].Cl[C:9]1[CH:16]=C[C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.C[N:18](C=O)C>O>[CH:1]1([CH2:4][O:5][C:12]2[CH:11]=[CH:10][C:9]([C:16]#[N:18])=[N:14][CH:13]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 121634-ChlorobenzonitrileHCID 24758Sodium hydrideHCID 75644Cyclopropanemethanol

Product 1

HCID 66803442HCID 66803442, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cyclopropylmethanol (0.120 mL, 1.504 mmol) was added to a suspension of sodium hydride (60% in mineral oil) (0.072 g, 1.805 mmol) in DMF (4 mL) at room temperature. The mixture was stirred at room temperature for 30 min, 4-chlorobenzonitrile (0.139 g, 1.002 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. The mixture was diluted with water and extracted with EtOAc (3 times). The organic extracts were combined, washed with water (2 times), brine (2 times), dried and evaporated under vacuum. The crude residue was purified by flash chromatography (hexane:EtOAc 9:1 to 85:15) to afford the title compound (0.120 g, 69%). Method B HPLC-MS: MH+ requires m/z=175. Found: m/z=175, Rt=1.73 min (100%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. extractionextracted with EtOAc (3 times)
  3. washwashed with water (2 times), brine (2 times)
  4. customdried
  5. customevaporated under vacuum
  6. customThe crude residue was purified by flash chromatography (hexane:EtOAc 9:1 to 85:15)

Sources & evidence

ORD record
ord-84ce9429a53245e0b7b6a4296a5c7fe3
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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