Boron trifluoride etherate → HCID 66670094, compound

HRID 1014919Notes

Reaction equation

HRID 1014919 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH:9]1[CH:21]=[CH:22][C:23](OCC)=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].B(F)(F)F.CCOCC.CC(C[AlH]CC(C)C)C.CCOC(C)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][Si:14]([C:17]([CH3:19])([CH3:18])[CH3:20])([CH3:16])[CH3:15])[CH:9]1[CH:21]=[CH:22][CH2:23][OH:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 66670181HCID 66670181, compound

Product 1

HCID 66670094HCID 66670094, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution containing 42 (8.6 g, 22 mmol) in DCM (80 ml) was cooled to −78° C. To this solution was slowly added boron trifluoride etherate (2.8 mL, 22 mmol) followed by the addition of 1M DIBALH in DCM (60 mL). The solution was stirred at −78° C. for 1 h. The reaction mixture was then treated with EtOAc and stirred for 30 min. The reaction mixture was allowed to warm to −5° C. The reaction was quenched by the dropwise addition of 1M HCl. The mixture was diluted with DCM and H2O and the layers were separated. The aqueous layer was extracted with DCM. The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford 8.5 g of 43 as a light yellow oil which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ5.70 (m, 1H), 5.59-5.55 (m, 1H), 4.16-4.13 (m, 2H), 4.05 (m, 2H), 3.72-3.35 (m, 4H), 1.95-1.88 (m, 2H), 1.77-1.67 (m, 2H), 1.48-1.44 (m, 9H), 0.88 (s, 9H), 0.08-0.03 (m, 6H) ppm.

Workup

  1. stirringstirred for 30 min
  2. temperatureto warm to −5° C
  3. customThe reaction was quenched by the dropwise addition of 1M HCl
  4. additionThe mixture was diluted with DCM and H2O
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with DCM
  7. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4ee91edbeed64659a82f9c0863111449
Source dataset
uspto-grants-2011_07
Patent number
US07985735B2

Reaction notes

Loading…