Triphenylphosphine → HCID 86600004, compound

HRID 748048Notes

Reaction equation

HRID 748048 reaction equation
[CH2:1]([CH:3]([CH2:19][CH3:20])[CH:4]([C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:9]=[CH:8][CH:7]=1)O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:66]=[N+:67]=[N-:68])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1.CCOC(C)=O>[N:66]([CH:4]([C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:9]=[CH:8][CH:7]=1)[CH:3]([CH2:19][CH3:20])[CH2:1][CH3:2])=[N+:67]=[N-:68]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68593443HCID 68593443, compound

Product 1

HCID 86600004HCID 86600004, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2-ethyl-1-[1-(4-methoxyphenyl)-1H-pyrazol-5-yl]butan-1-ol (1.0 g, 3.7 mmol) in THF (35 mL) at 0° C. was added triphenylphosphine (1.5 g, 5.6 mmol), diethyl azodicarboxylate (0.88 mL, 5.6 mmol) and diphenylphosphorylazide (1.2 mL, 5.6 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 18 h. The reaction mixture was diluted with EtOAc and washed twice with 1N HCl. The organic layer was dried (MgSO4), filtered, concentrated in vacuo and the resulting oil was purified by column chromatograhy (SiO2, EtOAc/ hexane, 1:9) to give a clear oil in 80% yield. 1H NMR (400 MHz, DMSO-d6) δ 7.66 (d, 1H, J=1.9 Hz), 7.32 (m, 2H), 7.07 (m, 2H), 6.55 (m, 1H), 4.42 (d, 1H, J=8.4 Hz), 3.80 (s, 3H), 1.60 (m, 1H), 1.41 (m, 1H), 1.25 (m, 1H), 1.14 (m, 2H), 0.69 (t, 3H, J=7.4 Hz), 0.60 (t, 3H, J=7.4 Hz).

Workup

  1. washwashed twice with 1N HCl
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customthe resulting oil was purified by column chromatograhy (SiO2, EtOAc/ hexane, 1:9)
  6. customto give a clear oil in 80% yield

Sources & evidence

ORD record
ord-d915a85c2b314d6eaf25d0e7f7258d8d
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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