(+)-2-Butanol → (S)-2-sec-Butoxy-6-nitrobenzonitrile

HRID 471649

Reaction equation

[CH3:1][C@H:2]([OH:5])[CH2:3][CH3:4].[N+:6]([C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([N+]([O-])=O)[C:10]=1[C:11]#[N:12])([O-:8])=[O:7]>>[C@@H:2]([O:5][C:13]1[CH:14]=[CH:15][CH:16]=[C:9]([N+:6]([O-:8])=[O:7])[C:10]=1[C:11]#[N:12])([CH2:3][CH3:4])[CH3:1]

Participants

Reactant 2

HCID 444683(+)-2-Butanol

HCID 520718Dinitrobenzonitrile

Product 1

HCID 67401509(S)-2-sec-Butoxy-6-nitrobenzonitrileYield 85.2%

Procedure

Prepared as in Example 111c from (S)-butan-2-ol and 2,6-dinitrobenzonitrile in 85.2% yield. 1H NMR (400 MHz, DMSO-d6) δ 0.94 (t, J=7.6 Hz, 3H), 1.29 (d, J=6.4 Hz, 1H), 1.69 (m, 2H), 4.72 (m, 1H), 7.74 (dd, J=6.8, 2.4 Hz, 1H), 7.86 (m, 1H).

Sources & evidence

ORD record: ord-ac4c376251014246b93e3336a4ef3f1d
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633186B2

Linked notes

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