Methanol → Methyl 3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolecarboxylate

HRID 1693664Notes

Reaction equation

HRID 1693664 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].C[O-].[Na+].CO.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[CH2:24][CH2:25][C:26](Cl)=[N:27]O>O1CCCC1>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[CH2:24][CH2:25][C:26]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:1]([CH:2]([CH3:4])[CH3:3])[O:5][N:27]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 2759969Methyl 4-methyl-3-oxopentanoateHCID 10942334Sodium MethoxideHCID 722650183-(2,6-dichlorophenyl)-N-hydroxypropanimidoyl chloride

Product 1

HCID 59264851Methyl 3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolecarboxylateYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl isobutyrylacetate (0.662 g, 5.8 mmol) in tetrahydrofuran (1.16 mL) was stirred at 0° C. as 0.5 N sodium methoxide in methanol solution (11.6 mL, 5.8 mmol) was added. A solution of 3-(2,6-dichlorophenyl)-N-hydroxypropanimidoyl chloride (1.04 g, 4.82 mmol) in tetrahydrofuran (3.8 mL) was added and the solution was allowed to warm to room temperature and was stirred overnight. The mixture was concentrated and the residue triturated with water and filtered to yield a white solid which was dried in a 45° C. oven with P2O5 under reduced pressure to yield the title compound (0.926 g, 56%). 1H NMR (DMSO-d6): 7.43 (d, J=8 Hz, 2H), 7.25 (t, J=8 Hz, 1H), 3.73 (s, 3H), 3.67 (septet, J=7 Hz, 1H), 3.24-3.20 (m, 2H), 3.07-3.03 (m, 2H), 1.23 (d, J=7 Hz, 6H).

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated
  3. customthe residue triturated with water
  4. filtrationfiltered
  5. customto yield a white solid which
  6. dry with materialwas dried in a 45° C. oven with P2O5 under reduced pressure

Sources & evidence

ORD record
ord-a8643dd8e84f46f1a1a375f8bfcb1daa
Source dataset
uspto-grants-2012_04
Patent number
US08158665B2

Reaction notes

Loading…