Ammonium Chloride → HCID 23079212, compound

HRID 1174017Notes

Reaction equation

HRID 1174017 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+].[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

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 66941337HCID 66941337, compound

Product 1

HCID 23079212HCID 23079212, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

The compound (4.56 g) obtained in Example 127-3 was dissolved in THF (136.8 ml). Then, the solution was added with a 1 mol/l K-Selectride® (manufactured by Aldrich Corporation)-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 separation/extraction with chloroform. The organic layer was washed with 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

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

Sources & evidence

ORD record
ord-bcd5b44fa1be49fe8f3379d5e25dec7a
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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