Triphenylphosphine → 3-(2-(4-(3-(2,6-Dichloro-phenyl)-5-isopropyl-3-H-(1,2,3)triazol-4ylmethyoxy)-2-methyl-phenyl)-vinyl)-benzoic acid methyl ester

HRID 424826Notes

Reaction equation

HRID 424826 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=2[CH3:19])[CH:5]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=1[N:29]1[C:33]([CH2:34]O)=[C:32]([CH:36]([CH3:38])[CH3:37])[N:31]=[N:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:34][C:33]3[N:29]([C:23]4[C:22]([Cl:21])=[CH:27][CH:26]=[CH:25][C:24]=4[Cl:28])[N:30]=[N:31][C:32]=3[CH:36]([CH3:38])[CH3:37])=[CH:14][C:13]=2[CH3:19])[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 45790389(1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanolHCID 667041783-(2-(4-Hydroxy-2-methyl-phenyl)-vinyl)-benzoic acid methyl ester

Product 1

HCID 1317294223-(2-(4-(3-(2,6-Dichloro-phenyl)-5-isopropyl-3-H-(1,2,3)triazol-4ylmethyoxy)-2-methyl-phenyl)-vinyl)-benzoic acid methyl esterYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-(4-hydroxy-2-methyl-phenyl)-vinyl)-benzoic acid methyl ester (0.09 4 g, 0.351 mmol) and (3-(2,6-dichloro-phenyl)-5-isopropyl-3H-(1,2,3)triazol-4-yl)-methanol (0.100 g, 0.351 mmol) in THF (3 mL) are added triphenylphosphine (0.184 g, 0.702 mmol) and diethyl azodicarboxylate (0.120 g, 0.720 mmol). The reaction is stirred overnight. The reaction is partitioned between ether and water. The organic layer is washed with brine and dried over sodium sulfate. The organic layers are filtered and concentrated. The crude solid is purified via flash chromatography using hexane:ethyl acetate (2:1) as eluent to give 3-(2-(4-(3-(2,6-Dichloro-phenyl)-5-isopropyl-3-H-(1,2,3)triazol-4ylmethyoxy)-2-methyl-phenyl)-vinyl)-benzoic acid methyl ester (0.04 g). ES/MS m/e (35Cl/37Cl) 535.8/538.2 (M+1).

Workup

  1. customThe reaction is partitioned between ether and water
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layers are filtered
  5. concentrationconcentrated
  6. customThe crude solid is purified via flash chromatography

Sources & evidence

ORD record
ord-b3fd944723f9480fbb458bd4f06dd84e
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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