2-Methyl-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-4-one → 2-Ethyl-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-4-one

HRID 521838Notes

Reaction equation

HRID 521838 reaction equation
CC1CC(=O)CCC(C2N(C)N=CC=2[N+]([O-])=O)O1.[CH3:19][N:20]1[C:24]([CH:25]2[O:32][C:29]3([CH2:31][CH2:30]3)[CH2:28][CH:27]([CH2:33][CH3:34])[O:26]2)=[C:23]([N+:35]([O-:37])=[O:36])[CH:22]=[N:21]1>>[CH2:31]([CH:29]1[CH2:28][C:27](=[O:26])[CH2:33][CH2:34][CH:25]([C:24]2[N:20]([CH3:19])[N:21]=[CH:22][C:23]=2[N+:35]([O-:37])=[O:36])[O:32]1)[CH3:30]

Participants

3

Reactant 2

HCID 867137742-Methyl-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-4-oneHCID 867137791-Methyl-5-(5-ethyl-6,8-dioxaspiro[2.5]octan-7-yl)-4-nitro-pyrazole

Product 1

HCID 867137802-Ethyl-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-4-one

Procedure

Following the procedure for Intermediate 5 starting from 1-methyl-5-(5-ethyl-6,8-dioxaspiro[2.5]octan-7-yl)-4-nitro-pyrazole gave 2-ethyl-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-4-one as a colourless solid (240 mg, 13% over two steps). 1H NMR (400 MHz, CDCl3) δ 8.04 (s, 1H), 5.67 (dd, J=11.0, 2.4 Hz, 1H), 4.02 (s, 3H), 3.94 (dd, J=10.2, 5.2 Hz, 1H), 3.04 (td, J=13.3, 3.3 Hz, 1H), 2.79-2.63 (m, 3H), 2.20-2.12 (m, 1H), 2.05-1.92 (m, 1H), 1.67-1.57 (m, 2H), 0.94 (t, J=7.4 Hz, 3H).

Sources & evidence

ORD record
ord-096aee47cd1842e29cb84fb4a85269ba
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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