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

HRID 1693669Notes

Reaction equation

HRID 1693669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]1[C:15]([CH2:16][OH:17])=[C:14]([CH:18]([CH3:20])[CH3:19])[O:13][N:12]=1.O[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[CH:34]=[C:33]([C:38]([O:40][CH3:41])=[O:39])[CH:32]=[CH:31]3)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[CH:34]=[C:33]([C:38]([O:40][CH3:41])=[O:39])[CH:32]=[CH:31]4)=[CH:26][CH:27]=2)=[C:14]([CH:18]([CH3:20])[CH3:19])[O:13][N:12]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 19834505Methyl 6-(4-hydroxyphenyl)-2-naphthoateHCID 59264863[3-[2-(2,6-Dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methanol

Product 1

HCID 24739328Methyl 6-[4-({[3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylateYield 24.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of [3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methanol (0.085 g, 0.27 mmol), methyl 6-(4-hydroxyphenyl)-2-naphthalenecarboxylate (0.075 g, 0.27 mmol), triphenyl phosphine (0.071 g, 0.27 mmol) and diisopropyl azodicarboxylate (0.049 mL, 0.27 mmol) in toluene (2.7 mL) was placed in microwave reaction tube and heated to 80° C. for 1000 seconds. The solution was concentrated and the residue dissolved in a solution of ethyl acetate and methanol, filtered and concentrated. The filtrate was purified by chromatography (silica gel, hexane to 3:7 ethyl acetate:hexanes) to provide the title compound (0.038 g, 24.5%). 1H NMR (DMSO-d6): 8.62 (s, 1H), 8.25 (s, 1H), 8.18 (d, J=9 Hz, 1H), 8.06 (d, J=9 Hz, 1H), 7.97 (dd, J=1, 9 Hz, 1H), 7.92 (dd, J=2, 9 Hz, 1H), 7.81 (d, J=9 Hz, 2H), 7.42 (d, J=8 Hz, 2H), 7.25 (t, J=8 Hz, 1H), 7.14 (d, J=9 Hz, 2H), 4.99 (s, 2H), 3.90 (s, 3H), 3.35 (septet, J=7 Hz, overlapping H2O 1H), 3.24-3.20 (m, 2H), 2.89-2.85 (m, 2H), 1.25 (d, J=7 Hz, 6H). ESI-LCMS m/z 574 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue dissolved in a solution of ethyl acetate and methanol
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe filtrate was purified by chromatography (silica gel, hexane to 3:7 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-9cdfcc54a574402ba7468432f10c1c87
Source dataset
uspto-grants-2012_04
Patent number
US08158665B2

Reaction notes

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