4-Oxazolecarboxylic acid, 5-[4-(trifluoromethyl)phenyl]-, ethyl ester → HCID 22473478, compound

HRID 1672584Notes

Reaction equation

HRID 1672584 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14](OCC)=[O:15])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][CH:12]=[N:11][C:10]=2[CH:14]=[O:15])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 27394814-Oxazolecarboxylic acid, 5-[4-(trifluoromethyl)phenyl]-, ethyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 22473478HCID 22473478, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of Example 52A (2.08 g, 7.29 mmol) in THF (20 mL) was cooled to −78° C. Diisobutylaluminum hydride (1.0 M in toluene, 14.6 mL, 14.6 mmol) was added slowly via syringe, and the reaction mixture was allowed to proceed 1 hr, then warmed to −20° C. After an additional 1 hr the reaction mixture was quenched with 1 N aq HCl, and the mixture was partitioned between Et2O and saturated aq NH4Cl solution. The separated aqueous phase was extracted with EtOAc, and the combined organic layer was washed with 3 N aq HCl and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified on silica gel (Analogix® Intelliflash 280™; SF40-150 g column; 15% to 55% EtOAc/hexanes, 30 min) to give 1.26 g (72%) of the title compound as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 10.07 (s, 1H), 8.75 (s, 1H), 8.30 (d, J=8.1, 2H), 7.97 (d, J=8.2, 2H). MS (DCI+) m/z 259 (M+NH4).

Workup

  1. customAfter an additional 1 hr the reaction mixture was quenched with 1 N aq HCl
  2. customthe mixture was partitioned between Et2O and saturated aq NH4Cl solution
  3. extractionThe separated aqueous phase was extracted with EtOAc
  4. washthe combined organic layer was washed with 3 N aq HCl and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified on silica gel (Analogix® Intelliflash 280™; SF40-150 g column; 15% to 55% EtOAc/hexanes, 30 min)

Sources & evidence

ORD record
ord-2efa17a9027c4144a782b54f53470c11
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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