Triphenylphosphine → 4-(1-Azidotridecyl)-2-triethylsilylfuran

HRID 1681508Notes

Reaction equation

HRID 1681508 reaction equation
C1C=CC(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)=CC=1.O[CH:19]([C:32]1[CH:33]=[C:34]([Si:37]([CH2:42][CH3:43])([CH2:40][CH3:41])[CH2:38][CH3:39])[O:35][CH:36]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N:15]([CH:19]([C:32]1[CH:33]=[C:34]([Si:37]([CH2:42][CH3:43])([CH2:40][CH3:41])[CH2:38][CH3:39])[O:35][CH:36]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 156632694-(1-Hydroxytridecyl)-2-triethylsilylfuran

Product 1

HCID 194331464-(1-Azidotridecyl)-2-triethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diphenylphosphonyl azide (143 mg, 0.52 mmol in THF (2 ml) was added over a period of 15 minutes to a solution of 4-(1-hydroxytridecyl)-2-triethylsilylfuran (200 mg, 0.52 mmol), triphenylphosphine (140 mg, 0.52 mmol) and diethyl azidocarboxylate (90 mg, 0.52 mmol) in THF (10 ml) at room temperature. After stirring for 2 days, the mixture was evaporated in the presence of a minimum amount of silica gel. The residue was purified by flash chromatography on silica using 5% ethyl ether/hexane to give the titled azide.

Workup

  1. customthe mixture was evaporated in the presence of a minimum amount of silica gel
  2. customThe residue was purified by flash chromatography on silica using 5% ethyl ether/hexane

Sources & evidence

ORD record
ord-261153e2d68b4a1b89bc0b759f461cfd
Source dataset
uspto-grants-1992_12
Patent number
US05171863

Reaction notes

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