Ethyl Acetate → HCID 54250138, compound

HRID 2369466Notes

Reaction equation

HRID 2369466 reaction equation
[CH2-]C(C)=O.C1N2CCN(CC2)C1.CCN(C(C)C)C(C)C.[CH3:22][Si:23]([CH2:26][CH2:27][O:28][CH2:29]Cl)([CH3:25])[CH3:24].[CH3:31][CH2:32][O:33][C:34](C)=[O:35]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:22][Si:23]([CH2:26][CH2:27][O:28][CH2:29][O:35][CH2:34][O:33][CH2:32][CH2:31][Si:23]([CH3:25])([CH3:24])[CH3:22])([CH3:25])[CH3:24]

Participants

8

Reactant 5

HCID 8857Ethyl AcetateHCID 9237DabcoHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178477758HCID 178477758, compound

Product 1

HCID 54250138HCID 54250138, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

The glycal alcohol 10 was prepared as described above by the irradiation of alkynyl diol 7 (2.0 g, 8.5 mmol) in toluene (0.20 M, 43 mL) with DABCO (1.9 g, 17 mmol) and W(CO)6 (750 mg, 2.1 mmol) for 20 hours. The crude mixture containing 10 was then dissolved in CH2Cl2 (1.0 M, 8.5 mL), and DIPEA (7.4 mL, 43 mmol) was added to the solution all at once. Then SEMCl (3.0 mL, 17 mmol) was carefully added to the reaction. The reaction was stirred at 40° C. for 3 hours. The reaction was then diluted with EtOAc (100 mL) and washed with H2O (3×50 mL). The organic layer was dried with MgSO4. After filtration, the volatiles were evaporated under reduced pressure, and chromatography (9:1 hexanes:EtOAc) provided glycal 13 (3:1 mixture of benzylidene acetal diastereomers) as a yellow oil (2.3 g, 75%).

Workup

  1. washwashed with H2O (3×50 mL)
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationAfter filtration
  4. customthe volatiles were evaporated under reduced pressure, and chromatography (9:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-1b2887bb6901478e9d17c5ecf476b579
Source dataset
uspto-grants-2014_04
Patent number
US08703977B2

Reaction notes

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