4-Cyanophenylboronic acid → 4-(4-oxotetrahydro-2H-pyran-3-yl)benzonitrile

HRID 2370200Notes

Reaction equation

HRID 2370200 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].I[CH:13]1[C:18](OC)([O:19]C)[CH2:17][CH2:16][O:15][CH2:14]1>>[O:19]=[C:18]1[CH2:17][CH2:16][O:15][CH2:14][CH:13]1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 580753843-iodo-4,4-dimethoxytetrahydro-2H-pyran

Product 1

HCID 580755704-(4-oxotetrahydro-2H-pyran-3-yl)benzonitrile

Procedure

4-cyanophenylboronic acid was reacted as described in Intermediate X(2) with 3-iodo-4,4-dimethoxytetrahydro-2H-pyran (Intermediate X(1)) to give 4-(4-oxotetrahydro-2H-pyran-3-yl)benzonitrile (Intermediate AA(2)). LC-MS (M+H)+=202.1. 1H NMR (500 MHz, CDCl3) δ ppm 7.66 (d, J=8.24 Hz, 2 H) 7.38 (d, J=8.55 Hz, 2 H) 4.23-4.31 (m, 2 H) 3.94-4.02 (m, 2 H) 3.85-3.92 (m, 1 H) 2.55-2.65 (m, 1 H) 2.52 (t, J=5.80 Hz, 1 H).

Sources & evidence

ORD record
ord-683972f48bfe45359993f5e6e4889095
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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