Tetrahydrofuran → HCID 59275582, compound

HRID 624316Notes

Reaction equation

HRID 624316 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[C:21]([O:27][CH:28]([CH3:30])[CH3:29])=[CH:20][C:13]=3[C:14]=2[C:15]([O:17]CC)=[O:16])=[CH:6][CH:5]=1.C1COCC1>O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:11][C:12]3[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[C:21]([O:27][CH:28]([CH3:30])[CH3:29])=[CH:20][C:13]=3[C:14]=2[C:15]([OH:17])=[O:16])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 56604953Ethyl 2-(4-fluorophenyl)-6-nitro-5-[(propan-2-yl)oxy]-1-benzofuran-3-carboxylate

Product 1

HCID 59275582HCID 59275582, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

An aqueous solution of sodium hydroxide (7.74 mL, 15.48 mmol, 2.0 M) was added to a mixture of ethyl 2-(4-fluorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-carboxylate (1.5 g, 3.87 mmol) in a THF (50 mL)/Water (10 mL) mixture at room temperature. The reaction mixture was heated to 50° C. and maintained at the same temperature overnight. The reaction mixture was then concentrated to remove the solvent. The residue was diluted with water, acidified with 1.5 N HCl, stirred for 5 min and filtered. The solid was dried under suction to obtained title compound as a white solid. Yield: 1.35 g, (97%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.35 (s, 1H) 8.02-8.16 (m, 2H) 7.78 (s, 1H) 7.33-7.49 (m, 2H) 4.69-4.85 (m, 1H) 1.27-1.40 (m, 6H).

Workup

  1. temperaturemaintained at the same temperature overnight
  2. concentrationThe reaction mixture was then concentrated
  3. customto remove the solvent
  4. additionThe residue was diluted with water
  5. filtrationfiltered
  6. customThe solid was dried under suction

Sources & evidence

ORD record
ord-3f9a6646ebc446e1970829435181d1db
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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