Isophorone → HCID 10612307, compound

HRID 2393929Notes

Reaction equation

[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1)([O-:13])=[O:12].C(C1C(O[SiH](C)C)=C(Br)C(OC)=CC=1CC1C(=O)C=CCC1(C)C)(C)(C)C>>[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][CH:9]2[C:2](=[O:1])[CH:3]=[C:4]([CH3:10])[CH2:5][C:6]2([CH3:8])[CH3:7])=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

Reactant 3

HCID 6544Isophorone

HCID 660114-Nitrobenzyl bromide

HCID 178488804HCID 178488804, compound

Product 1

HCID 10612307HCID 10612307, compound

Procedure

This compound was prepared from isophorone (2.065 g, 14.94 mmol) and p-nitrobenzyl bromide (4.06 g, 18.80 mmol, 1.25 equiv) in the manner previously described for the synthesis of enone (11), affording 1.891 g (46%), of the nitro-enone as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 0.98 and 1.13 (2s, 2×3H, geminal-CH3 's), 1.92 (s, 3H, 3-CH3), 2.17 and 231 (ABq, 2H, JAB =18.5 Hz, 4-H), 2.38 (dd, 1H, J=9.0, 3.3 Hz, 6-H), 2.75 and 3.05 (d of ABq, 2H, JAB =14.0 Hz, JA =3.2 Hz, JB =8.9 Hz, benzylic-CH2), 5.84 (s, 1H, 2-H), 7.33 and 7.53 ppm (ABq, 2H, JAB =8.2 Hz, Ar--H).

Workup

customaffording 1.891 g (46%)

Sources & evidence

ORD record: ord-96933ed8937745bc9fa6d186bef9cf1f
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808139

Reaction notes

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