Triphenylphosphine → HCID 86635956, compound

HRID 1698491Notes

Reaction equation

HRID 1698491 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:62]=[N+:63]=[N-:64])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1.O>[N:62]([CH:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)[C:2]([CH3:16])([CH3:15])[CH3:1])=[N+:63]=[N-:64]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67276267HCID 67276267, compound

Product 1

HCID 86635956HCID 86635956, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2,2-dimethyl-1-[4-(propylthio)phenyl)propan-1-ol (466 mg, 1.95 mmol) in THF (10 ml) were added triphenylphosphine (666 mg, 2.54 mmol), diethyl azodicarboxylate (0.40 ml, 2.54 mmol), and finally diphenylphosphoryl azide (0.55 ml, 2.54 mmol). The mixture was stirred at room temperature over for 3 days. Water (1 ml) was added and the mixture was evaporated. The residue was partitioned between ethyl acetate (50 ml) and water (30 ml). The organic phase was separated, washed with brine (30 ml), dried over MgSO4, filtered and evaporated to give an oil. The crude product was chromatographed on silica eluting with 4% EtOAc in hexanes to give the title product as a pale yellow oil (284 mg). 1H NMR δ (CDCl3) 7.29-7.27 (2H, m), 7.17-7.15 (2H, m), 4.23 (1H, s), 2.92 (2H, t, J=7.3 Hz), 1.73-1.67 (2H, m), 1.04 (3H, t, J=7.4 Hz), 0.90 (9H, s).

Workup

  1. customthe mixture was evaporated
  2. customThe residue was partitioned between ethyl acetate (50 ml) and water (30 ml)
  3. customThe organic phase was separated
  4. washwashed with brine (30 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil
  9. customThe crude product was chromatographed on silica eluting with 4% EtOAc in hexanes

Sources & evidence

ORD record
ord-21c0310cbb0d4fddbb154f7baf39ce54
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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