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

HRID 1693666Notes

Reaction equation

HRID 1693666 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)[C:34]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:33][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)[C:34]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:33][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 59264856Ethyl 6-(4-hydroxyphenyl)-1-naphthalenecarboxylateHCID 59264863[3-[2-(2,6-Dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methanol

Product 1

HCID 59264854Ethyl 6-[4-({[3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylateYield 55.8%

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 (0.110 g, 0.35 mmol) (from multiple batches), ethyl 6-(4-hydroxyphenyl)-1-naphthalenecarboxylate (0.102 g, 0.35 mmol), triphenylphosphine (0.092 g, 0.35 mmol) and diisopropyl azodicarboxylate (0.063 mL, 0.35 mmol) in toluene (3.5 mL) was placed in microwave reaction tube and heated to 80° C. for 1000 seconds. The solution was concentrated and purified by chromatography (silica gel, hexane to 1:4 ethyl acetate:hexanes) to provide the title compound (0.115 g, 51.6% as 0.7EtOAc). 1H NMR (DMSO-d6): 8.79 (d, J=9 Hz, 1H), 8.28 (s, 1H), 8.22 (d, J=8 Hz, 1H), 8.09 (d, J=7 Hz, 1H), 7.98 (dd, J=2, 9 Hz, 1H), 7.80 (d, J=9 Hz, 2H), 7.60 (m, 1H), 7.42 (d, J=8 Hz, 2H), 7.25 (t, J=8 Hz, 1H), 7.14 (d, J=8 Hz, 2H), 4.98 (s, 2H), 4.40 (q, J=7 Hz, 2H), 3.35 (septet, J=7 Hz, overlapping H2O, 1H), 3.24-3.20 (m, 2H), 2.89-2.85 (m, 2H), 1.37 (t, J=7 Hz, 3H), 1.25 (d, J=7 Hz, 6H). ESI-LCMS m/z 588 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by chromatography (silica gel, hexane to 1:4 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-b8908628cf1248e88c1e7d1a34b9e704
Source dataset
uspto-grants-2012_04
Patent number
US08158665B2

Reaction notes

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