5,6-Bis(nitrooxy)hexyl 4-nitrobenzoate → (2S)-4-hydroxybutane-1,2-diyl dinitrate

HRID 1361915Notes

Reaction equation

HRID 1361915 reaction equation
[N+](C1C=CC(C(OCCCCC(O[N+]([O-])=O)CO[N+]([O-])=O)=O)=CC=1)([O-])=O.[N+](C1C=CC(C([O:36][CH2:37][CH2:38][C@H:39]([O:45][N+:46]([O-:48])=[O:47])[CH2:40][O:41][N+:42]([O-:44])=[O:43])=O)=CC=1)([O-])=O>>[N+:42]([O-:44])([O:41][CH2:40][C@@H:39]([O:45][N+:46]([O-:48])=[O:47])[CH2:38][CH2:37][OH:36])=[O:43]

Participants

3

Reactant 2

HCID 765458355,6-Bis(nitrooxy)hexyl 4-nitrobenzoateHCID 86622534(3S)-3,4-bis(nitrooxy)butanyl 4-nitrobenzoate

Product 1

HCID 58812399(2S)-4-hydroxybutane-1,2-diyl dinitrate

Procedure

The title compound was prepared by following step B of the synthesis of intermediate 1, except that the reagent 5,6-bis(nitrooxy)hexyl 4-nitrobenzoate was replaced by (3S)-3,4-bis(nitrooxy)butanyl 4-nitrobenzoate. 1H NMR (300 MHz, CDCl3) δ 5.56 (ddd, J=2.8, 6.4, 13.0 Hz, 1H), 4.89 (dd, J=2.8, 13.0 Hz, 1H), 4.56 (dd, J=6.4, 13.0 Hz, 1H), 3.84 (td, J=2.7, 5.7 Hz, 2H), 2.02 (dd, J=5.7, 6.4 Hz, 2H), 1.73 (bs, 1H).

Sources & evidence

ORD record
ord-ad76177e414548eb8ea2e894228087bf
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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