Tetrahydrofuran → HCID 57550226, compound

HRID 1716853Notes

Reaction equation

HRID 1716853 reaction equation
[N:1]1([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][CH:19]=[C:20]([C:22]([O:24]C)=[O:23])[N:21]=3)=[CH:13][CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C1COCC1.[OH-].[Na+]>CO>[N:1]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[O:18][CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=3)=[CH:15][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57550197HCID 57550197, compound

Product 1

HCID 57550226HCID 57550226, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-[4-(1H-indol-1-ylmethyl)phenyl]-1,3-oxazole-4-carboxylate (1.52 g; 4.57 mmol) in (1:1) MeOH:THF was treated with sodium hydroxide (4.57 g, 4.57 mmol) stirred at room temperature overnight and concentrated under reduced pressure. The resultant concentrate was diluted with 1N sodium hydroxide (50 mL), washed with EtOAc, acidified with concentrated HCl and extracted with EtOAc. The extracts were combined, dried over MgSO4 and concentrated to dryness to give the title product in 91% yield, identified by NMR and mass spectral analyses. LCMS (ESI−) 317 (MH−).

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationThe resultant concentrate
  3. additionwas diluted with 1N sodium hydroxide (50 mL)
  4. washwashed with EtOAc
  5. extractionextracted with EtOAc
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-990df4a497374154aeb3f568ac70e6db
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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