2H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester → 3-(Oxan-4-yl)-3-oxopropanenitrile

HRID 871448Notes

Reaction equation

HRID 871448 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9]C)=O)[CH2:3][CH2:2]1.CC(C)C(=O)[CH2:14][C:15]#[N:16]>>[O:9]=[C:7]([CH:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)[CH2:14][C:15]#[N:16]

Participants

3

Reactant 2

HCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 101299214-Methyl-3-oxopentanenitrile

Product 1

HCID 629075903-(Oxan-4-yl)-3-oxopropanenitrileYield 24%

Procedure

Prepared from methyl tetrahydropyran-4-carboxylate (3 g, 20.80 mmol) according to the method described for 4-methyl-3-oxopentanenitrile in Example 122A Step 1, to afford 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanenitrile as a yellow oil (760 mg, 24%) which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 3.96-4.05 (m, 2H), 3.52 (s, 1H), 3.42-3.50 (m, 2H), 2.82 and 2.59 (2×m, 1H), 1.67-1.90 (m, 4H).

Sources & evidence

ORD record
ord-ff20d69ce8e543edb09fa6bbbe4d715a
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

Loading…