Phenylacetonitrile → (4-hydroxytetrahydro-2H-pyran-4-yl)(phenyl)acetonitrile

HRID 1943017Notes

Reaction equation

HRID 1943017 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[O:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1>C1COCC1>[OH:21][C:18]1([CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]#[N:9])[CH2:19][CH2:20][O:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178418339Butyllithium

Product 1

HCID 58415919(4-hydroxytetrahydro-2H-pyran-4-yl)(phenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To benzyl cyanide (1.970 ml, 19.39 mmol) was added THF (100 ml) and the solution cooled to −78° C. n-butyllithium (2.5 M in hexanes, 7.84 ml, 19.59 mmol) was added dropwise over 20 min via syringe pump and the solution stirred 30 min. Tetrahydro-4H-pyran-4-one (1.791 ml, 19.39 mmol) was added over 20 min via syringe pump and the solution stirred for 3 hours. The reaction was quenched by addition of ice-cold satd. NH4Cl and then partitioned between cold satd. NH4Cl and CH2Cl2. The aqueous portion was extracted 2×CH2Cl2, dried (Na2SO4), and concentrated in vacuo. Took up material in CH2Cl2 and allowed to crystallize over the weekend. The crystals were washed with diethyl ether and used without further purification. 3.14 g, 81%.

Workup

  1. additionwas added dropwise over 20 min via syringe pump
  2. stirringthe solution stirred for 3 hours
  3. customThe reaction was quenched by addition of ice-cold satd
  4. customNH4Cl and then partitioned between cold satd
  5. extractionThe aqueous portion was extracted 2×CH2Cl2
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto crystallize over the weekend
  9. washThe crystals were washed with diethyl ether
  10. customused without further purification

Sources & evidence

ORD record
ord-fa325875bb1449e088ee8dfd454fa441
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

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