Boron trifluoride etherate → HCID 18340684, compound

HRID 1369230Notes

Reaction equation

HRID 1369230 reaction equation
B(F)(F)F.CCOCC.O[C:11]1([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][C:14]2[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:13]=2[CH2:12]1.C([SiH](CC)CC)C>C(Cl)Cl.C(O)C.[Pd]>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:13]2[CH2:12][CH:11]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][C:14]=2[CH:22]=1

Participants

7

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 18340685HCID 18340685, compound

Product 1

HCID 18340684HCID 18340684, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride etherate (0.48 mL, 3.9 mmole) was added to a solution of ethyl (±)-10,11-dihydro-10-hydroxy-3-methoxydibenzo[b,f]oxepine-10-acetate (690 mg, 1.95 mmole) and triethylsilane (0.62 mL, 3.9 mmole) in dry CH2Cl2 at 0° C. under argon. After 20 min, the reaction was quenched with 5% NaHCO3, and the mixture was extracted with CH2Cl2. Drying (MgSO4) and concentration gave a yellow oil. This was dissolved in absolute ethanol (20 mL) and 10% Pd/C (413 mg, 0.39 mmole) was added. The mixture was hydrogenated for 3 hr at 50 psi on a Parr hydrogenation apparatus. The catalyst was removed by filtration through celite®, and the filtrate was concentrated to afford the title compound (523 mg, 86%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ7.18-6.58 (m, 7 H), 4.18-4.08 (m, 2 H), 3.80 (s, 3 H), 3.80-3.74(m, 1 H), 3.40-3.30 (dd, 1 H). 2.98-2.84 (dd, 1 H), 2.74-2.62 (dd, 1 H), 2.60-2.52(m, 1 H), 1.32-1.20 (t, 3 H).

Workup

  1. customthe reaction was quenched with 5% NaHCO3
  2. extractionthe mixture was extracted with CH2Cl2
  3. customDrying
  4. concentration(MgSO4) and concentration
  5. customgave a yellow oil
  6. waitThe mixture was hydrogenated for 3 hr at 50 psi on a Parr hydrogenation apparatus
  7. customThe catalyst was removed by filtration through celite®
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1db85665af674460b4f63bb0b9b75907
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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