Diethyl Ether → HCID 18470629, compound

HRID 2228515Notes

Reaction equation

HRID 2228515 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[C:4]([F:7])([F:6])[F:5].[C:9]([C:11]1[C:16]([F:17])=[CH:15][C:14]([O:18][CH3:19])=[CH:13][C:12]=1F)#[N:10].C(OCC)C>CN(C)C=O.O1CCCC1>[C:9]([C:11]1[C:12]([O:8][CH2:3][C:4]([F:7])([F:6])[F:5])=[CH:13][C:14]([O:18][CH3:19])=[CH:15][C:16]=1[F:17])#[N:10]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 27787722,6-Difluoro-4-methoxybenzonitrile

Product 1

HCID 18470629HCID 18470629, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.6 g, 60%, 0.040 mol) was added to a solution of trifluoroethanol (4.0 g, 0.040 mol) in dimethylformamide (50 ml) and the solution stirred for 90 minutes. This solution was then added to 4-cyano-3,5-difluoroanisole [Grey et al, Mol Cryst Liq Cryst, 172, 165-189 (1989)] (6.30 g, 0.037 mol) in tetrahydrofuran (50 ml) and the reaction stirred at room temperature for 2 hours. The reaction mixture was poured into diethyl ether (250 ml) washed with water (2×150 ml) and then brine (50 ml). The organic layer was dried (MgSO4), filtered and evaporated under reduced pressure, then triturated with diethyl ether:hexane to give the subtitle compound as white crystals (5.92 g, 59%). Rf 0.14 (dichloromethane:hexane, 1:2, v/v). MS m/z 267 (MNH4)+.

Workup

  1. stirringthe reaction stirred at room temperature for 2 hours
  2. washwashed with water (2×150 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-3dc984c899954a218166ea5a2b5c3b56
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

Loading…