Triphenylphosphine → HCID 131731865, compound

HRID 74988Notes

Reaction equation

HRID 74988 reaction equation
O[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([O:8][CH3:9])[CH:3]1[O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P([N:65]=[N+:66]=[N-:67])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:65]([CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([O:8][CH3:9])[CH:3]1[O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[N+:66]=[N-:67]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5363146Diisopropyl azodicarboxylateHCID 67286790HCID 67286790, compound2×

Product 1

HCID 131731865HCID 131731865, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic [1-Hydroxy-3-methoxy-2-cyclohexanoxy]tert-butyl-dimethylsilane, 51f, (2.5 g; 9.6 mmol) in 60 mL of dry THF at room temperature was added, triphenylphosphine (5.0 g; 19.2 mmol), DIAD (3.9 g; 19.2 mmol) and diphenylphosphoryl azide (5.3 g; 19.2 mmol) and the reaction mixture was stirred at room temperature for 60 h. The solvent was concentrated in vacuo and the resultant oil was purified by silica gel chromatography (10% Et2O-Hexane to ether gradient) to afford 2.57 g of the desired product 51g.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe resultant oil was purified by silica gel chromatography (10% Et2O-Hexane to ether gradient)

Sources & evidence

ORD record
ord-cdbac8c59621462c9324a2b38553e435
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

Loading…