Water → HCID 86663497, compound

HRID 1950714Notes

Reaction equation

HRID 1950714 reaction equation
O1CCOCC1.O.[Cl:8][C:9]1[CH:10]=[C:11]([C:17]2([C:36]([F:39])([F:38])[F:37])[O:21][N:20]=[C:19]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]([C:32]([O:34]C)=[O:33])=[CH:24][CH:23]=3)[CH2:18]2)[CH:12]=[C:13]([Cl:16])[C:14]=1[F:15].[Li]>CCCCCCC.CCOC(C)=O>[Cl:8][C:9]1[CH:10]=[C:11]([C:17]2([C:36]([F:37])([F:39])[F:38])[O:21][N:20]=[C:19]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]([C:32]([OH:34])=[O:33])=[CH:24][CH:23]=3)[CH2:18]2)[CH:12]=[C:13]([Cl:16])[C:14]=1[F:15]

Participants

7

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 3028194LithiumHCID 86663498HCID 86663498, compound

Product 1

HCID 86663497HCID 86663497, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

To a 7:1 dioxane:water mixture (80 mL) containing methyl 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthoate (Preparation 6, 2.9 g, 5.9 mmol) was added lithium hydroixide (430 mg, 18.0 mmol). The reaction mixture was allowed to stir at room temperature for 3 hours. Thin layer chromatography (TLC) 25:75 EtOAc:heptane showed consumption of starting material. 1N HCl (25 mL) was added. The reaction was partitioned between water (25 mL) and ethyl acetate (150 mL). The organic phase was collected, dried over Na2SO4, and concentrated under vacuum to give a solid (2.77 g, 98%). 1H NMR (CDCl3) δ ppm: 9.10 (1H), 8.82 (1H), 8.34 (1H), 7.76-7.66 (4H), 7.60 (1H), 4.32 (1H), 3.93 (1H).

Workup

  1. customconsumption of starting material
  2. addition1N HCl (25 mL) was added
  3. customThe reaction was partitioned between water (25 mL) and ethyl acetate (150 mL)
  4. customThe organic phase was collected
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-092700d07b6f40b385b5c7e9e333004f
Source dataset
uspto-grants-2013_03
Patent number
US08404649B2

Reaction notes

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