Citric Acid → (5-{[6-(5-Methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrophenyl)methanol

HRID 2080678Notes

Reaction equation

HRID 2080678 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[CH:16][C:17]([N+:23]([O-:25])=[O:24])=[C:18]([CH:22]=3)[C:19](O)=[O:20])=[CH:9][CH:8]=2)[N:3]=1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[CH:16][C:17]([N+:23]([O-:25])=[O:24])=[C:18]([CH2:19][OH:20])[CH:22]=3)=[CH:9][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 671105555-{[6-(5-Methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrobenzoic acid

Product 1

HCID 67110993(5-{[6-(5-Methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrophenyl)methanolYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

282 mg of N,N′-carboxydiimidazole was added to a tetrahydrofuran (5 ml) solution of 399 mg of the above carboxylic acid, and stirred at room temperature for 30 minutes. With cooling with ice, the above reaction liquid was added to an aqueous 5 ml solution of 219 mg of sodium borohydride, and stirred for 20 minutes. This was neutralized with aqueous 10% citric acid solution added thereto, then extracted with ethyl acetate, the organic layer was dried, and the solvent was evaporated away under reduced pressure to obtain 367 mg of (5-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrophenyl)methanol as a pale yellow solid.

Workup

  1. temperatureWith cooling with ice
  2. customthe above reaction liquid
  3. stirringstirred for 20 minutes
  4. additionadded
  5. extractionextracted with ethyl acetate
  6. customthe organic layer was dried
  7. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-cb45d1ea5d2c44ac90bda83737b48302
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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