Triphenylphosphine → HCID 58117375, compound

HRID 1406423Notes

Reaction equation

HRID 1406423 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].[C:11]1([C@H:17](O)[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.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>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C@H:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:18])[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 6375161-Phenylethanol, (R)-

Product 1

HCID 58117375HCID 58117375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 20 mL microwave vial was charged with 1H-pyrazole-4-carboxylic acid ethyl ester (1 g, 7.1 mmol), (R)-1-phenylethanol (1.31 mL, 10.7 mmol), triphenylphosphine (3 g, 11.4 mmol) and tetrahydrofuran (15 mL). The reaction was stirred at ambient temperature for 10 minutes before adding diisopropyl azodicarboxylate (2.25 mL, 11.14 mmol) with cooling. The vial was heated under microwave irradiation at 140° C. for 15 mins. After cooling, the solvent was removed in vacuo and the residue purified by flash chromatography on SiO2 with hexane—30% ethyl acetate/hexane (gradient) to afford intermediate (6f), 1((S)-1-Phenyl-ethyl)-1H-pyrazole-4-carboxylic acid ethyl ester as an oil, 1.646 g, 94%.

Workup

  1. temperaturewith cooling
  2. temperatureThe vial was heated under microwave irradiation at 140° C. for 15 mins
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customthe residue purified by flash chromatography on SiO2 with hexane—30% ethyl acetate/hexane (gradient)

Sources & evidence

ORD record
ord-cdd300a24e514cabab63a85ba76df773
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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