Hydrochloric Acid → HCID 66572420, compound

HRID 75844Notes

Reaction equation

HRID 75844 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([C:20]([O:22]CC)=[O:21])[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[O:17][N:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66572312HCID 66572312, compound

Product 1

HCID 66572420HCID 66572420, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To Ethyl 3-(4-(benzyloxy)phenyl)isoxazole-5-carboxylate (900 mg) in THF (18 ml), 1M aqueous solution of NaOH (13.9 ml) was added and the reaction mixture was stirred for 20 minutes. It was acidified with 1 Molar hydrochloric acid and extracted with ethyl acetate. Organic layer was collected and dried over Na2SO4 and concentrated to obtain pale yellow solid, which was crystallized using EtOAc—petroleum ether to obtain the title compound as off white solid. Yield: 765 mg (93%); MS (ES+): m/z 296 (M+1); 1H NMR (DMSO-d6; 300 MHz): δ 7.91 (d, 2H), 7.73 (s, 1H), 7:34-7.48 (m, 5H), 7.17 (d, 2H), 5.19 (s, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. customOrganic layer was collected
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto obtain pale yellow solid, which
  6. customwas crystallized

Sources & evidence

ORD record
ord-d2cac0e2788045d99912140f8284ab1e
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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