Triphenylphosphine → HCID 57965599, compound

HRID 1930794Notes

Reaction equation

HRID 1930794 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([OH:22])[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:42][O:43][C:44]([C:46]1[S:47][C:48]([C:52]([O:54][CH3:55])=[O:53])=[CH:49][C:50]=1O)=[O:45]>C1COCC1>[CH3:42][O:43][C:44]([C:46]1[S:47][C:48]([C:52]([O:54][CH3:55])=[O:53])=[CH:49][C:50]=1[O:22][CH:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[Cl:13])[CH3:21])=[O:45]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 260821-(2-Chlorophenyl)ethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3056832,5-Dimethyl 3-hydroxythiophene-2,5-dicarboxylate

Product 1

HCID 57965599HCID 57965599, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.29 g, 7.41 mmol, 1.3 Eq.) was added to a stirred solution of 1-(2-Chloro-phenyl)-ethanol (893 mg, 5.70 mmol, 1.0 Eq.), triphenylphosphine (1.94 g, 7.41 mmol, 1.3 Eq.) and 3-hydroxythiophene-2,5-dicarboxylic acid dimethyl ester (1.23 g, 5.70 mmol, 1.0 Eq.) in anhydrous THF (20 mL) at 0° C. under nitrogen and the reaction allowed to warm to ambient temperature overnight. The crude reaction mixture was concentrated in vacuo and purified by column chromatography (10% EtOAc/Petroleum ether) to give the sub-title compound as a white solid (1.94 g, 5.6 mmol, 93%); 1H NMR (400 MHz, CDCl3) δ 1.71 (3H, d), 3.89 (3H, s), 3.95 (3H, s), 5.80 (1H, q), 7.20-7.32 (3H, m), 7.39 (1H, d), 7.66 (1H, d).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by column chromatography (10% EtOAc/Petroleum ether)

Sources & evidence

ORD record
ord-a6d4fe7028bd4b7ead67088eb9e3aa75
Source dataset
uspto-grants-2012_05
Patent number
US08188134B2

Reaction notes

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