Methanol → HCID 58498028, compound

HRID 536444Notes

Reaction equation

HRID 536444 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[O:12][C:11]([CH3:14])=[N:10][C:9]=2[C:8]([C:15]2[CH2:19][C:18]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].CO>O1CCCC1.Cl.C(OCC)(=O)C>[Cl:30][C:28]1[CH:29]=[C:24]([C:18]2([C:20]([F:22])([F:21])[F:23])[O:17][N:16]=[C:15]([C:8]3[C:9]4[N:10]=[C:11]([CH3:14])[O:12][C:13]=4[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=3)[CH2:19]2)[CH:25]=[C:26]([Cl:31])[CH:27]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 58497930HCID 58497930, compound

Product 1

HCID 58498028HCID 58498028, compoundYield 79.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl)-2-methyl-benzo[d]oxazole-7-carboxylic acid methyl ester (2.75 g) in tetrahydrofuran (50 ml) was added aqueous sodium hydroxide (1M) (8.7 ml) and methanol (5 ml). The reaction mixture was stirred at ambient temperature for 2.5 hours. The reaction mixture was diluted with aqueous hydrochloric acid (1M) (150 ml) and ethyl acetate (200 ml) and the phases separated. The organic phase was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: 1-6% v/v methanol in dichloromethane) to give 4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl)-2-methyl-benzo[d]oxazole-7-carboxylic acid (2.12 g) as yellow solid. 1H-NMR (400 MHz, CDCl3): 8.05-7.43 (m, 5H), 4.57 (d, 1H), 4.13 (d, 1H), 2.79 (s, 3H) ppm.

Workup

  1. customthe phases separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (eluent: 1-6% v/v methanol in dichloromethane)

Sources & evidence

ORD record
ord-c299dcf9da0c4ab1b61ad494ae197edf
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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