Thionyl Chloride → phenyl(tetrahydro-4H-pyran-4-ylidene)acetonitrile

HRID 1943018Notes

Reaction equation

HRID 1943018 reaction equation
O[C:2]1([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]#[N:10])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.O=S(Cl)Cl>N1C=CC=CC=1>[C:11]1([C:8](=[C:2]2[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)[C:9]#[N:10])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58415919(4-hydroxytetrahydro-2H-pyran-4-yl)(phenyl)acetonitrile

Product 1

HCID 58415944phenyl(tetrahydro-4H-pyran-4-ylidene)acetonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(4-hydroxytetrahydro-2H-pyran-4-yl)(phenyl)acetonitrile (500 mg, 2.301 mmol) was dissolved in pyridine (10 ml). SOCl2 (1.680 ml, 23.01 mmol) was added and the reaction was stirred for 25 minutes then concentrated in vacuo. The crude material was purified by silica gel chromatography on an Isco Companion (5 to 35% EA/hexanes over 20 min, 40 g silica column). The desired fractions were combined and concentrated in vacuo. 450 mg, 98%.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude material was purified by silica gel chromatography on an Isco Companion (5 to 35% EA/hexanes over 20 min, 40 g silica column)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a0c7199ed194c5595efd928c09ab9d0
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

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