3-Furanol, tetrahydro- → HCID 66747016, compound

HRID 1467195Notes

Reaction equation

[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.[O:15]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]1>>[N+:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([O:20][CH:17]2[CH2:18][CH2:19][O:15][CH2:16]2)[C:5]=1[C:6]#[N:7])([O-:14])=[O:13]

Participants

Reactant 2

HCID 99603-Furanol, tetrahydro-

HCID 520718Dinitrobenzonitrile

Product 1

HCID 66747016HCID 66747016, compoundYield 50%

Procedure

Prepared as in Example 166d of WO 2008/154221 from 2,6-dinitrobenzonitrile and tetrahydrofuran-3-ol in 50% yield as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 2.04 (m, 1H), 2.32 (m, 1H), 3.81 (td, J=8.3, 4.6 Hz, 1H), 3.89 (m, 2H), 3.98 (dd, J=10.8, 4.5 Hz, 1H), 5.36 (m, 1H), 7.75 (dd, J=8.1, 1.5 Hz, 1H), 7.91 (t, J=8.2 Hz, 1H), 7.95 (dd, J=8.2, 1.6 Hz, 1H).

Sources & evidence

ORD record: ord-b020f0c1f8dd488ca016e4c71c8ac093
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000054B2

Reaction notes

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