Triphenylphosphine → Methyl 3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate

HRID 2423466Notes

Reaction equation

HRID 2423466 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[SH:9].O[CH2:11][C:12]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([CH:21]([CH3:23])[CH3:22])[O:14][N:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9][CH2:11][C:12]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([CH:21]([CH3:23])[CH3:22])[O:14][N:13]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 90671Benzenethiol, 2,6-dichloro-HCID 97268Di-tert-butyl azodicarboxylateHCID 59321585HCID 59321585, compound

Product 1

HCID 59321546Methyl 3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dichlorobenzenethiol (530 mg, 2.96 mmol), methyl 3-(hydroxymethyl)-5-(1-methylethyl)-4-isoxazolecarboxylate (629 mg, 2.46 mmol) and triphenylphosphine (1.29 g, 4.93 mmol) in dichloromethane (20 mL) was added di-tert-butyl azodicarboxylate (1.14 g, 4.93 mmol). The solution was stirred at ambient temperature overnight. The solution was then adsorbed onto silica gel and purified by chromatography (silica gel, 0-100% ethyl acetate in hexanes gradient elution) to afford methyl 3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl) -4-isoxazolecarboxylate (886 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ 7.52-7.35 (m, 3H), 4.18 (s, 3H), 3.72 (s, 2H), 3.64 (septet, J=7 Hz, 1H), 1.20 (d, J=7 Hz, 6H). LRMS (APCI) m/z 360 (M+H)+.

Workup

  1. custompurified by chromatography (silica gel, 0-100% ethyl acetate in hexanes gradient elution)

Sources & evidence

ORD record
ord-c7ddf24e99e94215849b6c1ff3b902ff
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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