Boron trifluoride etherate → HCID 12381653, compound

HRID 520395Notes

Reaction equation

HRID 520395 reaction equation
[O:1]=[C:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:9][C:10]([CH3:15])([CH2:13]O)[CH2:11][OH:12].B(F)(F)F.CCOCC>C(#N)C>[CH3:8][C:2]1([C:3]([O:5][CH2:6][CH3:7])=[O:4])[O:12][CH2:11][C:10]([CH3:15])([CH3:13])[CH2:9][O:1]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12041Ethyl pyruvateHCID 31344Neopentyl glycol

Product 1

HCID 12381653HCID 12381653, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 2-oxopropanoate (0.581 g, 5 mmol) and 2,2-dimethylpropane-1,3-diol (0.521 g, 5.00 mmol) in acetonitrile (5 mL) cooled to 0° C. was added BF3.OEt2 (0.063 mL, 0.500 mmol), and the mixture was allowed to warm to rt and stirred at rt for 18 h. The reaction mixture was quenched with sat. NaHCO3 (5 mL) and diluted with ether/hexane (1:1, 20 mL). The organic layer was washed with water, brine and dried (MgSO4). The solvent was evaporated to yield ethyl 2,5,5-trimethyl-1,3-dioxane-2-carboxylate as a clear oil (681 mg). 1H NMR (500 MHz, CDCl3) δ ppm 4.31 (2H, q, J=7.07 Hz), 3.48-3.58 (4H, m), 1.55 (3H, s), 1.35 (3H, t, J=7.17 Hz), 1.22 (3H, s), 0.69-0.75 (3H, m). Ethyl 2,5,5-trimethyl-1,3-dioxane-2-carboxylate (90 mg) was saponified (1 N NaOH, MeOH-THF) to afford Cap P-24 (69 mg). 1H NMR (500 MHz, CDCl3) δ ppm 3.53-3.64 (4H, m), 1.63 (3H, s), 1.23 (3H, s), 0.78 (3H, s).

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3 (5 mL)
  2. additiondiluted with ether/hexane (1:1, 20 mL)
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-fddba20930ba4ab89986447a400bcb2b
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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