Boron trifluoride etherate → Methyl 2-methyl-5-{3-[(5-methyl-2-phenyloxazol-4-yl)methyl]benzyl}-1,3-dioxane-2-carboxylate

HRID 890671Notes

Reaction equation

HRID 890671 reaction equation
[OH:1][CH2:2][CH:3]([CH2:24][OH:25])[CH2:4][C:5]1[CH:6]=[C:7]([CH:21]=[CH:22][CH:23]=1)[CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14].[C:26]([O:31][CH3:32])(=[O:30])[C:27]([CH3:29])=O.B(F)(F)F.CCOCC.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:29][C:27]1([C:26]([O:31][CH3:32])=[O:30])[O:1][CH2:2][CH:3]([CH2:4][C:5]2[CH:23]=[CH:22][CH:21]=[C:7]([CH2:8][C:9]3[N:10]=[C:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:12][C:13]=3[CH3:14])[CH:6]=2)[CH2:24][O:25]1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11748Methyl pyruvateHCID 516892Sodium BicarbonateHCID 218666464-{3-[2,2-Bis(hydroxymethyl)ethyl]benzyl}-5-methyl-2-phenyloxazole

Product 1

HCID 21866902Methyl 2-methyl-5-{3-[(5-methyl-2-phenyloxazol-4-yl)methyl]benzyl}-1,3-dioxane-2-carboxylateYield 49.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 5 ml of acetonitrile, 297 mg of 4-{3-[2,2-bis-(hydroxymethyl)ethyl]benzyl}-5-methyl-2-phenyloxazole and 369 mg of methyl pyruvate were added. To the mixture was added 544 mg of boron trifluoride etherate (about 47% ) with stirring at room temperature, and stirred for 14 hours at room temperature. The reaction solution was poured into an ice-cold water solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=3:1) to provide 185 mg of a mixture (cis:trans=2.5:1, based on NMR integral value) as colorless oil.

Workup

  1. stirringstirred for 14 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-6ae22c66728541839f5e5c33b26ac2b4
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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