5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carbaldehyde → 1-{5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethanol

HRID 2045951Notes

Reaction equation

HRID 2045951 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2([C:25]([F:28])([F:27])[F:26])[O:16][N:15]=[C:14]([C:17]3[S:21][C:20]([CH:22]=[O:23])=[C:19]([CH3:24])[CH:18]=3)[CH2:13]2)[CH:8]=[C:9]([Cl:11])[CH:10]=1>O1CCCC1>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2([C:25]([F:27])([F:26])[F:28])[O:16][N:15]=[C:14]([C:17]3[S:21][C:20]([CH:22]([OH:23])[CH3:1])=[C:19]([CH3:24])[CH:18]=3)[CH2:13]2)[CH:8]=[C:9]([Cl:11])[CH:10]=1

Participants

4

Reactant 2

HCID 866812905-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 665872011-{5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromid (1.80 ml, 3M in diethyl ether) is added to a solution of 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carbaldehyde (Example 1, (ii) step B, 2 g) in tetrahydrofuran (39 ml) under nitrogen at 0° C. The mixture is slowly warmed to room temperature and stirred overnight. After 21 hours, the reaction is quenched with a saturated aqueous solution of NH4Cl in water. The mixture is extracted two times with ethyl acetate. The organic phases are combined, dried over MgSO4 and concentrated in vacuo to yield 1-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethanol (2.1 g) as a yellowish foam. The crude product obtained is used without further purification. MS (HPLC/MS): 424 (MH+). Retention time: 2.03 min.

Workup

  1. waitAfter 21 hours
  2. customthe reaction is quenched with a saturated aqueous solution of NH4Cl in water
  3. extractionThe mixture is extracted two times with ethyl acetate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23039785acb54dc58abfb720e9f4c0ee
Source dataset
uspto-grants-2013_11
Patent number
US08592418B2

Reaction notes

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