Triphenylphosphine → HCID 178444930, compound

HRID 871046Notes

Reaction equation

HRID 871046 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:6]([CH2:8]O)[CH:7]=1.[C:17]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(O[C:41](/[N:43]=[N:44]/[C:45](OC(C)(C)C)=O)=[O:42])(C)C>C1COCC1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:6]([CH:7]=1)[CH2:8][N:44]1[CH:45]=[CH:17][C:41]([OH:42])=[N:43]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 82928937HCID 82928937, compound

Product 1

HCID 178444930HCID 178444930, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A solution of [5-bromo-2-(2-ethyl-butoxy)-phenyl]-methanol, 2, (1.2 g 4.2 mmol), triphenylphosphine (1.6 g, 6 mmol), di-tert-butylazodicarboxylate (1.4 g, 6 mmol) and 3-methylpyrazolyl-5-one (0.75 g, 7.7 mmol) in a mixture of THF (5 mL) and toluene (10 ml) was heated at 120° C. in an Emrys microwave reactor for 20 min. The volatiles were removed in vacuo. The crude product was purified on silica to yield 1-[5-bromo-2-(2-ethyl-butoxy)-benzyl]-1H-pyrazol-3-ol, 3.

Workup

  1. customThe volatiles were removed in vacuo
  2. customThe crude product was purified on silica

Sources & evidence

ORD record
ord-32e8cbb216c244d59038b251d0d78b9d
Source dataset
uspto-grants-2015_03
Patent number
US08969589B2

Reaction notes

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