HCID 22493731, compound → HCID 22493724, compound

HRID 1816403Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:14](=O)[C:15]2[CH:20]=[C:19]([CH2:21][CH2:22][CH3:23])[C:18]([O:24][CH3:25])=[CH:17][C:16]=2[CH2:26][CH2:27][CH3:28])=[C:7]([O:9][N:10]=C(C)C)[CH:8]=1>C(#N)C.Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:14]([C:15]3[CH:20]=[C:19]([CH2:21][CH2:22][CH3:23])[C:18]([O:24][CH3:25])=[CH:17][C:16]=3[CH2:26][CH2:27][CH3:28])=[N:10][O:9][C:7]=2[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A red mixture of acetone O-[5-methoxy-2-(4-methoxy-2,5-dipropylbenzoyl)phenyl]oxime (2.30 g, 5.79 mmol) in acetonitrile (43 mL) and 5% aqueous HCl (32 mL) was stirred at 80° C. for 4 h. Most of the acetonitrile was removed in vacuo and extraction was conducted in CH2Cl2 (3×60 mL) with 33% saturated brine (50 mL). Flash chromatography with silica gel (gradient to 8% EtOAc/hexanes) provided the title compound as a colorless oil (1.72 g, 87% yield for two steps): 1H NMR (300 MHz, CDCl3) δ 0.84 (t, 3H, J=7.3 Hz), 0.96 (t, 3H, J=7.4 Hz), 1.58 (m, 4H), 2.60 (t, 2H, J=7.6 Hz), 2.70 (t, 2H, J=7.8 Hz), 3.89 (s, 3H), 3.92 (s, 3H), 6.84 (s, 1H), 6.92 (dd, 1H, J=8.7, 2.1 Hz), 7.05 (d, 1H, J=2.0 Hz), 7.23 (s, 1H), 7.40 (d, 1H, J=8.7 Hz); MS m/e 340 (M+H)+.

Workup

customMost of the acetonitrile was removed in vacuo and extraction

Sources & evidence

ORD record: ord-6e0071b374244f70a1b53d2e2eadf09d
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884814B2

Reaction notes

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