Water → 4-(3,4-Dichlorophenyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 1749154Notes

Reaction equation

HRID 1749154 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10].Cl[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Cl.O>CS(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([C:12]#[N:13])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8115Bis(2-chloroethyl) etherHCID 24758Sodium hydrideHCID 76690(3,4-Dichlorophenyl)acetonitrile

Product 1

HCID 431642774-(3,4-Dichlorophenyl)tetrahydro-2H-pyran-4-carbonitrileYield 35.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

NaH (420 mg, 10.5 mmol, 60%, w/w) was added to a solution of 2-(3,4-dichlorophenyl)acetonitrile (930 mg, 5 mmol) in DMSO (20 ml) at room temperature. After stirring for 40 minutes at room temperature (15° C.), 1-chloro-2-(2-chloroethoxy)ethane (786.5 mg, 5.5 mmol) was added. The mixture was stirred for another 1 hour, then poured into water (5.0 mL), and the mixture was extracted with EtOAc-toluene (2:1, 3×30 mL). The combined organic extracts were washed with 2N aq. HCl (30 mL), water (30 mL) and brine (30 mL), dried over MgSO4, filtered, and concentrated to 5 mL. The precipitated solids were collected by filtration and washed with cold diethylether (10 mL) to afford the title compound (450 mg, yield 35%). 1H NMR (400 MHz, CDCl3): 7.58 (d, J=2.0 Hz, 1H), 7.52 (d, J=1.6 Hz, 1H), 7.34 (dd, J=2.0 Hz, J=8.8 Hz, 1H), 4.08-4.12 (m, 2H), 3.85-3.92 (m, 2H), 2.2.02-2.13 (m, 4H). LC-MS (M+H): m/z 229.1 (M-CN).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc-toluene (2:1, 3×30 mL)
  3. washThe combined organic extracts were washed with 2N aq. HCl (30 mL), water (30 mL) and brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to 5 mL
  7. filtrationThe precipitated solids were collected by filtration
  8. washwashed with cold diethylether (10 mL)

Sources & evidence

ORD record
ord-63c47c8fdf9b4131bb5e33c9fb96e007
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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