Ammonium Chloride → HCID 23079212, compound

HRID 2080734Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6](=[CH:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5]2.CCC(C)[BH-](C(C)CC)C(C)CC.[K+].C1COCC1.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:5]2

Participants

Conditions

Temperature: -78 °C

Procedure

The compound (4.56 g) obtained in Example 11-3 was dissolved in THF (136 ml). Then, the solution was added with a 1 mol/l K-Selectride/THF solution (8.76 ml) while being stirred at −78° C., followed by stirring at the same temperature for 1 hour. The reaction solution was added with a saturated aqueous ammonium chloride solution and then subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (hexane/diethyl ether), thereby obtaining the subject compound (2.03 g) as a yellow oily substance.

Workup

stirringby stirring at the same temperature for 1 hour
extractionsubjected to extraction with chloroform
washThe organic layer was washed with a saturated saline solution
dry with materialdried with anhydrous sodium sulfate
concentrationfollowed by concentration under reduced pressure
customThe residue was purified through silica gel column chromatography (hexane/diethyl ether)

Sources & evidence

ORD record: ord-e181e0631d5d45b58c53d26fd5e992cf
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932281B2

Reaction notes

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