Triphenylphosphine → HCID 76613006, compound

HRID 1785436Notes

Reaction equation

HRID 1785436 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16][CH:17](O)[CH3:18])[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:67]=[N+:68]=[N-:69])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1.ClCCl>[N:67]([CH:17]([CH3:18])[CH2:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[N+:68]=[N-:69]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 199401P,P-Diphenylphosphinic azideHCID 69064193HCID 69064193, compound

Product 1

HCID 76613006HCID 76613006, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 1-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-propan-2-ol (130 mg, 0.46 mmol) in THF (1.5 mL) under nitrogen at 0° C. was added diisopropyl azodicarboxylate (140 mg, 0.7 mmol), triphenylphosphine (180 mg, 0.7 mmol), and diphenylphosphoryl azide (190 mg, 0.7 mmol) and the mixture was stirred at 0° C. for 15 min. The mixture was diluted with dichloromethane, washed with water, brine, dried over magnesium sulfate, and purified by flash column chromatography (ethyl acetate/hexanes). 1H NMR (CDCl3) 7.27 (m, 1H), 7.2 (m, 1H), 7.16 (s, 1H), 7.08 (m, 1H), 4.74 (s, 2H), 3.65 (m, 1H), 2.82 (dd, 1H), 2.73 (dd, 1H), 1.25 (d, 3H), 0.94 (s, 9H), 0.10 (s, 6H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. custompurified by flash column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ede011a0f2824c2d9586f37aeb9e12dc
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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