(-)-3-Hydroxytetrahydrofuran → HCID 58464882, compound

HRID 2089358Notes

Reaction equation

HRID 2089358 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[OH:11][C@@H:12]1[CH2:16][CH2:15][O:14][CH2:13]1>>[CH3:7][N:6]1[C:2]([O:11][C@@H:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[C:3]([N+:8]([O-:10])=[O:9])[CH:4]=[N:5]1

Participants

3

Reactant 2

HCID 641512(-)-3-HydroxytetrahydrofuranHCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazole

Product 1

HCID 58464882HCID 58464882, compoundYield 34%

Procedure

Following the procedure for Example 230 starting with 5-chloro-1-methyl-4-nitro-1H-pyrazole and (R)-(−)-3-hydroxy tetrahydrofuran gave (R)-1-methyl-4-nitro-5-(tetrahydrofuran-3-yloxy)-1H-pyrazole as a clear oil (90 mg, 34%). 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 5.65 (q, J=3.4 Hz, 1H), 4.10 (q, J=8.0 Hz, 1H), 4.02-3.87 (m, 2H), 3.81 (dd, J=11.3, 3.4 Hz, 1H), 3.71 (s, 3H), 2.26 (td, J=7.3, 3.4 Hz, 2H)

Sources & evidence

ORD record
ord-7890f775192b4e09a3b95a4c208e7836
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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