Triethylsilane → HCID 22734068, compound

HRID 2084768Notes

Reaction equation

HRID 2084768 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][CH:9]([C:11]1[C:16]2[CH:17]([CH3:20])[CH2:18][O:19][C:15]=2[C:14]([O:21][CH3:22])=[CH:13][CH:12]=1)O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][CH2:9][C:11]1[C:16]2[CH:17]([CH3:20])[CH2:18][O:19][C:15]=2[C:14]([O:21][CH3:22])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 22733899HCID 22733899, compound

Product 1

HCID 22734068HCID 22734068, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, a solution (28 ml) of Compound 56a (1.0 g) obtained in Step A in methylene chloride was cooled to −78° C., and then boron trifluoride ether complex (0.69 ml) and triethylsilane (1.35 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=50/1) to give Compound 56 (0.62 g, 64.9%) as pale-yellow oily crystals.

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=50/1)

Sources & evidence

ORD record
ord-816f277804da48e79b985737e4d62ac9
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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