3-Furanol, tetrahydro- → HCID 86723171, compound

HRID 868885Notes

Reaction equation

HRID 868885 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[N+:11]([O-:13])=[O:12].O[CH:15]1[CH2:19][CH2:18][O:17][CH2:16]1>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:15]1[CH2:19][CH2:18][O:17][CH2:16]1)[CH:6]=[C:5]2[N+:11]([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 99603-Furanol, tetrahydro-HCID 86723162HCID 86723162, compound

Product 1

HCID 86723171HCID 86723171, compoundYield 18%

Procedure

The title compound was prepared from 5-fluoro-3-nitro-indole and 3-hydroxytetrahydrofuran in 18% yield according to the general procedure for Preparation 31A. The minor isomer was not isolated or characterized. 1H NMR (400 MHz, CDCl3): δ 2.21-2.27 (1H, m), 2.60-2.69 (1H, m), 3.95-4.01 (1H, m), 4.05-4.09 (1H, m), 4.20-4.25(2H, m), 5.07-5.10 (1H, m), 7.13 (1H, td, J=2.4, 8.8 Hz), 7.44 (1H, dd, J=4.0, 8.8 Hz), 7.98 (1H, dd, J=2.4, 9.2 Hz), 8.28 (1H, s).

Workup

  1. customThe minor isomer was not isolated

Sources & evidence

ORD record
ord-36eb007baa094f399d5ee44942097d95
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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