Triphenylphosphine → 4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole

HRID 1487663Notes

Reaction equation

HRID 1487663 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4](O)[CH2:3][CH2:2]1.[N+:8]([C:11]1[CH:12]=[N:13][NH:14][CH:15]=1)([O-:10])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N+:8]([C:11]1[CH:12]=[N:13][N:14]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:15]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 74956Tetrahydro-4H-pyran-4-olHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 591862964-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazoleYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of tetrahydro-2H-pyran-4-ol (1 equiv), 4-nitro-1H-pyrazole (1 equiv) and triphenylphosphine (1.2 equiv) in THF (1.0 M) was added diisopropyl azodicarboxylate (1.5 equiv) in THF (2.0 M) at 0° C. The mixture was stirred at room temperature overnight. The crude product was purified by silica gel chromatography (2.5% MeOH in DCM) to afford the desired product (23% yield) as a white solid. MS (ESI) m/z 198.1 [M+H]+.

Workup

  1. customThe crude product was purified by silica gel chromatography (2.5% MeOH in DCM)

Sources & evidence

ORD record
ord-127625a3e89d42c89eaccc9869c9bbb3
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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