Triphenylphosphine → 3-(4-Iodopyrazol-1-yl)-2,2-dimethylpropionic acid methyl ester

HRID 2279840Notes

Reaction equation

HRID 2279840 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[CH3:7][O:8][C:9](=[O:15])[C:10]([CH3:14])([CH3:13])[CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:7][O:8][C:9](=[O:15])[C:10]([CH3:14])([CH3:13])[CH2:11][N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 770224-IodopyrazoleHCID 84152Methyl 3-hydroxypivalateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 678164023-(4-Iodopyrazol-1-yl)-2,2-dimethylpropionic acid methyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-iodo-1H-pyrazole (194 mg, 1 mmol), 3-hydroxy-2,2-dimethylpropionic acid methyl ester (200 mg, 1.5 mmol) and triphenylphosphine (393 mg, 1.5 mmol) in THF (5 mL) was treated with DIAD (0.3 mL, 1.5 mmol) at room temperature. After 2 h, the reaction mixture was concentrated and the crude residue was purified by column chromatography (SiO2, 10% ethyl acetate/hexanes) to give 249 mg (81%) of desired product as an oil. 1H NMR (500 MHz, CDCl3) δ 7.59 (s, 1H), 7.46 (s, 1H), 3.69 (s, 2H), 3.55 (s, 3H), 1.18 (s, 6H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe crude residue was purified by column chromatography (SiO2, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bd48eef52e454ccc87f4656b42b4f568
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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