Triethylsilane → HCID 22734057, compound

HRID 2084769Notes

Reaction equation

HRID 2084769 reaction equation
O[CH:2]([C:10]1[C:15]2[CH:16]([CH3:19])[CH2:17][O:18][C:14]=2[C:13]([O:20][CH3:21])=[CH:12][CH:11]=1)[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:21][O:20][C:13]1[C:14]2[O:18][CH2:17][CH:16]([CH3:19])[C:15]=2[C:10]([CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 22734356HCID 22734356, compound

Product 1

HCID 22734057HCID 22734057, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, a solution (17 ml) of Compound 57a (0.6 g) obtained in Step A in methylene chloride was cooled to −78° C., and then boron trifluoride ether complex (0.42 ml) and triethylsilane (0.8 ml) were successively added thereto, followed by stirring at 0° C. for 2 hours. The reaction solution was poured into a saturated aqueous solution of sodium bicarbonate and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to give Compound 57 (0.042 g, 9.1%) as a pale-yellow oily substance.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with a saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-688111b5af1f45cc907ba7094275508c
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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