Triphenylphosphine → HCID 56631310, compound

HRID 1598431Notes

Reaction equation

HRID 1598431 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@@H:12](O)[C@H:11]([CH3:16])[O:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.P([N:64]=[N+:65]=[N-:66])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O>C1COCC1>[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:64]=[N+:65]=[N-:66])[C@H:11]([CH3:16])[O:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123414Diphenylphosphoryl azideHCID 5462977Diethyl azodicarboxylateHCID 11010263HCID 11010263, compound

Product 1

HCID 56631310HCID 56631310, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the alcohol from step 3 herein (62 mg, 0.25 mmol) in dry THF (2.5 ml), at room temperature, under argon, were added successively Ph3P (66 mg, 1 eq.), DEAD (40 μl, 1 eq.) and (PhO)2 PON3 (54 μl, 1 eq.) and the solution was stirred for 18 hours. The THF was evaporated and the crude oil was purified by flash chromatography (silica gel, 95:5 hexanes/EtOAc) to give 38 mg (56%) of the titled azide as a clear oil.

Workup

  1. customThe THF was evaporated
  2. customthe crude oil was purified by flash chromatography (silica gel, 95:5 hexanes/EtOAc)

Sources & evidence

ORD record
ord-118208b395b045b182a41ebe1a297f72
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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