Isobutyl nitrate → HCID 19900817, compound

HRID 1029767Notes

Reaction equation

[C:1]([C:5]1([C:13]2[S:14][C:15]([S:18][CH2:19]C(O)=O)=[CH:16][CH:17]=2)[O:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].[N+:23]([O-])([O:25]CC(C)C)=[O:24]>>[C:1]([C:5]1([C:13]2[S:14][C:15]([S:18][CH2:19][N+:23]([O-:25])=[O:24])=[CH:16][CH:17]=2)[O:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 10974Isobutyl nitrate

HCID 19900761HCID 19900761, compound

Product 1

HCID 19900817HCID 19900817, compoundYield 47%

Procedure

Using a similar nitration procedure to that described in Example 9, but starring from acid (C) and using isobutyl nitrate in place of isoamyl nitrate, there was obtained 2-t-butyl-5,5-dimethyl- 2-[2-(nitromethylthio)thien-5-yl]-1,3-dioxane (D) as an oil, in 47% yield; NMR: 0.6(s, 3H), 0.96(s, 9H), 1.2(s, 3H), 3.36(dd, 2H), 3.55(d, 2H), 5.32(s, 2H), 6.82(d, 1H), 7.22(d, 1H); m/e (chemical ionisation) 346 (M+H)+.

Sources & evidence

ORD record: ord-5892e5be6db04a3c9705a018c7628fcc
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102905

Reaction notes

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