Methanol → HCID 11592416, compound

HRID 2355141Notes

Reaction equation

HRID 2355141 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:16][C:15]([C:17]4[C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=5[O:19][C:18]=4[CH2:26][CH2:27][CH2:28][CH3:29])=[N:14][CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:30][CH2:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38]C)=[O:37])=[CH:34][CH:33]=1.[OH-].[Na+].CO.O>C1COCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:16][C:15]([C:17]4[C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=5[O:19][C:18]=4[CH2:26][CH2:27][CH2:28][CH3:29])=[N:14][CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([C:36]([OH:38])=[O:37])=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 68452332HCID 68452332, compound

Product 1

HCID 11592416HCID 11592416, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-[({1-bromo-6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)methyl]benzoate (77.2 mg, 0.126 mmol), prepared in the previous step, and 1 N NaOH (200 μL, 0.200 mmol) in 15 mL of THF, plus 15 mL of methanol, plus 5 mL of water was refluxed under nitrogen for 21 h. After cooling to room temperature the reaction was filtered and acidified by the addition of 300 μL of 1 N HCl. The reaction was concentrated under reduced pressure to remove most of the THF and methanol. The solid present was collected by filtration and dried under reduced pressure to give the title compound (61 mg, 81%) as a white solid, mp 281-283° C. Elemental Analysis for C33H26BrNO5. 0.05 H2O Calc'd: C, 66.35; H, 4.40; N, 2.34. Found: C, 66.50; H, 4.34; N, 2.18.

Workup

  1. temperaturewas refluxed under nitrogen for 21 h
  2. filtrationwas filtered
  3. additionacidified by the addition of 300 μL of 1 N HCl
  4. concentrationThe reaction was concentrated under reduced pressure
  5. customto remove most of the THF and methanol
  6. filtrationThe solid present was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-36db9087a88f40e19f4b4f4cc8ace31e
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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