Boron trifluoride etherate → HCID 17789168, compound

HRID 530540Notes

Reaction equation

HRID 530540 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1.B(F)(F)F.CCOCC>CCOC(C)=O>[CH:13]1([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8079CyclohexeneHCID 8434Ethylparaben

Product 1

HCID 17789168HCID 17789168, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4-hydroxybenzoate (1.0 g, 6.02 mmol) and cyclohexene (6.0 mL) were mixed together and boron trifluoride diethyl etherate (0.38 mL, 3.01 mmol) was then added. The mixture was heated under reflux for 2 h and then cooled to rt. EtOAc (20 mL) was added and the solution washed with 5% NaOH solution (3×40 mL) and with H2O (50 mL). The organic layer was dried over Na2SO4 and the solvent was evaporated. The crude product was absorbed over silica gel and purified by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:EtOAc (from 100:0 to 90:10) to afford the title compound (1.17 g, 78%), as white solid. MS (ESI) m/z: 249 [M−H]+; 1H NMR (DMSO-d6): δ 1.29 (t, J=7.1 Hz, 3H), 1.33-1.49 (m, 5H), 1.50-1.59 (m, 1H), 1.63-1.79 (m, 2H), 1.89-1.98 (m, 2H), 4.26 (q, J=7.1 Hz, 2H), 4.41-4.49 (m, 1H), 7.02 (d, J=8.8 Hz, 2H), 7.87 (d, J=8.8 Hz, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. washthe solution washed with 5% NaOH solution (3×40 mL) and with H2O (50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe crude product was absorbed over silica gel
  7. custompurified by column chromatography
  8. washeluting with Cy

Sources & evidence

ORD record
ord-94252dd1cc1a4a09a0ad5392b14ac50a
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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