Triethylsilane → HCID 69543777, compound

HRID 2084766Notes

Reaction equation

O[C:2]([C:16]1[C:21]2[CH2:22][C:23]([CH3:26])([CH3:25])[O:24][C:20]=2[C:19]([O:27][CH3:28])=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[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:36](=O)(O)[O-:37].[Na+]>C(Cl)Cl>[CH3:36][O:37][C:19]1([O:27][CH3:28])[C:20]2[O:24][C:23]([CH3:25])([CH3:26])[CH2:22][C:21]=2[C:16]([CH:2]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:3][C:4]2[CH:5]=[CH:6][N:7]=[CH:8][CH:9]=2)=[CH:17][CH2:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

Under an argon atmosphere, a solution of Compound 47a (0.4 g) obtained in Step A in methylene chloride (3 ml) was cooled to −78° C., and then boron trifluoride ether complex (0.3 ml) and triethylsilane (0.52 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 47 (0.27 g, 56.7%) as a yellowish brown oily substance.

Workup

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

Sources & evidence

ORD record: ord-f707b7c5f8f3415495169e0fa6753824
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716987B1

Reaction notes

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