Triphenylphosphine → HCID 18403411, compound

HRID 1017269Notes

Reaction equation

HRID 1017269 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]1([CH3:27])[CH:18]=[CH:17][C:16]([S:19]([O:22][CH2:23][CH:24]([OH:26])[CH3:25])(=[O:21])=[O:20])=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:47][C:48]1[CH:53]=[C:52]([O:54][C:55]([F:58])([F:57])[F:56])[CH:51]=[CH:50][C:49]=1O>>[I:47][C:48]1[CH:53]=[C:52]([O:54][C:55]([F:56])([F:57])[F:58])[CH:51]=[CH:50][C:49]=1[O:26][CH:24]([CH3:25])[CH2:23][O:22][S:19]([C:16]1[CH:15]=[CH:14][C:13]([CH3:27])=[CH:18][CH:17]=1)(=[O:20])=[O:21]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27694112-Iodo-4-(trifluoromethoxy)phenolHCID 10998810HCID 10998810, compound

Product 1

HCID 18403411HCID 18403411, compoundYield 109.8%

Procedure

Diethyl azodicarboxylate (5 ml, 31.8 mmol) was added dropwise to a stirred solution of (p-toluenesulphonyloxy)propan-2-ol (Description 19; 7.6 g, 33 mmol), triphenylphosphine (9.0 g, 34 mmol) and 2-iodo-4-trifluoromethoxyphenol (10 ml, 33 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate) to give the title compound (18.7 g).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate)

Sources & evidence

ORD record
ord-ff14962da70247c884734841c7cdefae
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

Loading…