Tetrahydro-3-furanmethanol → HCID 66745604, compound

HRID 1467206Notes

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.[OH:15][CH2:16][CH:17]1[CH2:21][CH2:20][O:19][CH2:18]1>>[N+:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([O:15][CH2:16][CH:17]2[CH2:21][CH2:20][O:19][CH2:18]2)[C:5]=1[C:6]#[N:7])([O-:14])=[O:13]

Participants

Reactant 2

HCID 139980Tetrahydro-3-furanmethanol

HCID 520718Dinitrobenzonitrile

Product 1

HCID 66745604HCID 66745604, compoundYield 48%

Procedure

Prepared as in Example 160d from 2,6-dinitrobenzonitrile and 3-hydroxymethyltetrahydrofuran in 48% yield as an orange-red solid. 1H NMR (400 MHz, DMSO-d6) δ 1.68 (m, 1H), 2.00 (m, 1H), 2.70 (m, 1H), 3.54 (m, 1H), 3.66 (m, 1H), 3.76 (m, 2H), 4.03 (m, 1H), 4.19 (m, 1H), 7.73 (d, J=7.6 Hz, 1H), 7.90-7.95 (m, 2H).

Sources & evidence

ORD record: ord-4c16526b0f904e20b6f7e062a49e2939
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000054B2

Reaction notes

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