Boron trifluoride etherate → HCID 15073127, compound

HRID 1837083Notes

Reaction equation

HRID 1837083 reaction equation
B(F)(F)F.CC[O:7][CH2:8][CH3:9].OCC[C:13]#[C:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.C(=O)(O)[O-:26].[Na+]>C(O)C1C=CC=CC=1.[Hg]=O>[CH2:18]([O:17][C:15]1[CH2:14][CH2:13][O:7][C:8](=[O:26])[CH:9]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 15073126Benzyl 5-hydroxypent-2-ynoate

Product 1

HCID 15073127HCID 15073127, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 244Benzyl AlcoholSolvent2×

Conditions

Temperature
60 °C

Procedure

A heterogeneous mixture of benzyl alcohol (2.65 mole, 274.4 mL), mercury(II) oxide (red) (13.26 mmol, 2.87 g) and boron trifluoride diethyl etherate (0.133 mole, 16.3 mL) was heated at 60° C. for 3 hours (eventually turned homogeneous). A solution of the product from Example 31C (90.17 g, 0.442 mole) in benzyl alcohol (91.5 mL) was added at ambient temperature, and the reaction mixture was stirred at 70° C. for 4 hours and again at ambient temperature overnight. It was poured into an aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified via flash chromatography (silica, hexane to hexane:ethyl acetate, 30:1 to 1:2) to provide the title compound as a white solid (49.6 g, 55%). 1H NMR (300 MHz, CDCl3) δ 2.60 (t, 2H), 4.38 (t, 2H), 4.95 (s, 2H), 5.28 (s, 1H), 7.32-7.46 (m, 5H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography (silica, hexane to hexane:ethyl acetate, 30:1 to 1:2)

Sources & evidence

ORD record
ord-c632c3d6c3e6420f99d07531fffe3a8b
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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