Boric Acid → HCID 10511055, compound

HRID 570088Notes

Reaction equation

HRID 570088 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].B(O)(O)O.[CH2:13](O)[CH2:14][C:15]#C.C(OC)(=O)CC(C)=O.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[O:4]=[C:3]([CH3:5])[CH2:2][C:1]([O:7][CH2:8][CH2:15][C:14]#[CH:13])=[O:6]

Participants

6

Reactant 4

HCID 7628Boric AcidHCID 7757Methyl acetoacetateHCID 135663-Butyn-1-OLHCID 86686465HCID 86686465, compound

Product 1

HCID 10511055HCID 10511055, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl acetoacetate (1 g, 8.6 mmol) was dissolved in 40 mL dry toluene. Boric acid (53 mg, 0.86 mmol) and 3-butyn-1-ol (1 g, 14.3 mmol) were added to the methyl acetoacetate/toluene solution under a N2 atmosphere and the mixture was refluxed for 24 hr using a Dean-Stark condenser. Solvents were then removed under reduced pressure. The crude product was purified by flash column chromatography (SiO2, hexane/ethylacetate:15/1) to obtain compound 2 (950 mg, 73% yield), a pale yellow to colorless liquid. 1H NMR 300 MHz (ppm, CDCl3): 4.21 (2H, t J=6.8 Hz), 3.48 (2H, s), 2.59-2.54 (2H, dt J=6.8, 2.7 Hz), 2.29 (3H, s), 2.00 (1H, t J=2.7). 13C NMR (CDCl3, 75 MHz): 200.22, 166.83, 79.70, 70.12, 62.99, 49.92, 30.16, 18.89. ESI-MS: (M+H)+=m/z 155.18 (calculated MW of C8H10O3: 154.16 Da).

Workup

  1. temperaturethe mixture was refluxed for 24 hr
  2. customSolvents were then removed under reduced pressure
  3. customThe crude product was purified by flash column chromatography (SiO2, hexane/ethylacetate:15/1)

Sources & evidence

ORD record
ord-f1affff496f34b37a9a0bf474336e217
Source dataset
uspto-grants-2015_05
Patent number
US09023653B2

Reaction notes

Loading…