Triphenylphosphine → Methyl 6-[2-chloro-4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylate

HRID 1693648Notes

Reaction equation

HRID 1693648 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=[CH:12]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([Cl:49])[C:44]=1[C:50]1[C:54]([CH2:55]O)=[C:53]([CH:57]([CH3:59])[CH3:58])[O:52][N:51]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:55][C:54]2[C:50]([C:44]3[C:43]([Cl:42])=[CH:48][CH:47]=[CH:46][C:45]=3[Cl:49])=[N:51][O:52][C:53]=2[CH:57]([CH3:59])[CH3:58])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=[CH:12]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanolHCID 59264873HCID 59264873, compound

Product 1

HCID 59264865Methyl 6-[2-chloro-4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylateYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 6-(2-chloro-4-hydroxyphenyl)-1-naphthalenecarboxylate (0.25 g, 0.799 mmol), polymer-bound triphenylphosphine (0.27 g, 0.799 mmol), [3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methanol (0.23 g, 0.799 mmol) and 10 mL of dichloromethane was cooled to 0° C. Diisopropyl azodicarboxylate (0.16 mL, 0.799 mmol) was slowly added to the reaction mixture. The reaction mixture was stirred for 10 minutes at the above temperature and then warmed to room temperature and stirred for 18 h. The reaction mixture was filtered and the filtrate was concentrated to give oil. The crude material was partially purified by flash chromatography over silica gel using 20% EtOAc in hexane to afford 0.36 g of the title compound. 1H NMR (DMSO-d6): 8.75 (d, J=9 Hz, 1H), 8.22 (d, J=8 Hz, 1H), 8.14 (d, J=7 Hz, 1H), 8.0 (s, 1H), 7.53-7.67 (m, 5H), 7.36 (d, J=8.6 Hz, 1H), 7.03-7.04 (m, 1H), 6.84-6.87 (m, 1H), 4.92 (s, 2H), 3.93 (s, 3H), 3.46 (m, 1H), 1.34 (m, 6H).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 18 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customto give oil
  6. customThe crude material was partially purified by flash chromatography over silica gel using 20% EtOAc in hexane

Sources & evidence

ORD record
ord-da8586c18a314693b3947173c09303ff
Source dataset
uspto-grants-2012_04
Patent number
US08158665B2

Reaction notes

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