Water → methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate

HRID 1184849Notes

Reaction equation

HRID 1184849 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:2].[H-].[Na+].Cl[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Cl.O>CS(C)=O>[C:1]([C:3]1([C:4]2[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8115Bis(2-chloroethyl) etherHCID 24758Sodium hydrideHCID 10821136Methyl 3-(cyanomethyl)benzoate

Product 1

HCID 57441036methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of methyl 3-(cyanomethyl)benzoate 1 (2 g, 11.4 mmol) in DMSO (20 mL) was added NaH (60%, 959 mg, 24.0 mmol) portion wise over 10 min. The reaction mixture was stirred for 40 min at rt and then bis(2-chloroethyl)ether (1.27 mL, 10.9 mmol) was added slowly and stirring continued for 18 hours. The reaction was poured into water and extracted with EtOAc/toluene (2:1). The combined extracts were washed with 2N HCl solution, water, brine, dried and evaporated the crude methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate 80 (1.25 g, 44%).

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. extractionextracted with EtOAc/toluene (2:1)
  4. washThe combined extracts were washed with 2N HCl solution, water, brine
  5. customdried
  6. customevaporated the crude methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate 80 (1.25 g, 44%)

Sources & evidence

ORD record
ord-e778aa5714d24adca6047b4b683b1ff9
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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