Triphenylphosphine → HCID 58525266, compound

HRID 409423Notes

Reaction equation

HRID 409423 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15]([C:17]1[S:18][CH:19]=[CH:20][C:21]=1[OH:22])=[O:16].[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30](O)[CH3:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30]([O:22][C:21]1[CH:20]=[CH:19][S:18][C:17]=1[C:15]([O:14][CH3:13])=[O:16])[CH3:31]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 260821-(2-Chlorophenyl)ethanolHCID 5811273-Hydroxy-thiophene-2-carboxylic acid methyl esterHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 58525266HCID 58525266, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (2.6 mL, 16.4 mmol, 1.3 Eq.) was added dropwise to a stirred solution of methyl-3-hydroxythiophene-2-carboxylate (2.0 g, 12.6 mmol, 1.0 Eq.), 1-(2-chlorophenyl)ethanol (2.57 g, 16.4 mmol, 1.3 Eq.) and triphenylphosphine (4.31 g, 16.4 mmol, 1.3 Eq.) in ahydrous THF (30 mL) at 0° C. under nitrogen. The reaction was allowed to warm to ambient temperature overnight. The crude reaction mixture was absorbed onto SiO2 and purified by column chromatography eluting with 0 to 10% EtOAc/petroleum ether to give the sub-title compound as a white solid (1.89 g, 6.37 mmol, 50%); 1H NMR (400 MHz, CDCl3) δ 1.72 (3H, d), 3.87 (3H, s), 5.78 (1H, quint), 6.65 (1H, d), 7.21-7.32 (3H, m), 7.38 (1H, dd), 7.55 (1H, dd).

Workup

  1. customThe crude reaction mixture
  2. customwas absorbed onto SiO2
  3. custompurified by column chromatography
  4. washeluting with 0 to 10% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-f512810bda1b4b48a2d4db2377e56cb2
Source dataset
uspto-grants-2014_06
Patent number
US08759389B1

Reaction notes

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