Ammonium Chloride → HCID 22033041, compound

HRID 1792402Notes

Reaction equation

HRID 1792402 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]I)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]C(C)(C)C.[CH3:24][O:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30](=[O:43])[C:31]([CH3:42])([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)[CH2:32][O:33]2)=[CH:28][CH:27]=1.[NH4+].[Cl-]>CCCCC.C(OCC)C.C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:30]1([OH:43])[C:29]2[C:34](=[CH:35][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)[O:33][CH2:32][C:31]1([CH3:42])[C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 22033069HCID 22033069, compoundHCID 22033454HCID 22033454, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 22033041HCID 22033041, compoundYield 75.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 9-(t-butyldimethylsilyloxy)nonyl iodide (1.05 g, 2.7 mmol) in pentane (10 ml) and diethylether (7 ml) was added at −78° C. t-BuLi (1.64M in pentane, 3.62 ml, 5.94 mmol), which was stirred for 10 minutes and then stirred for 1 h at room temperature. The mixture was cooled to −78° C. again, and a solution of 7-methoxy-3-methyl-3-(3-pyridyl)chroman-4-one (436 mg, 1.62 mmol) dissolved in THF (5 ml) was added thereto. The resulting solution was stirred at −78° C. for 30 minutes, and then stirred for 1 h at room temperature. The reaction solution was neutralized under ice-cooling using saturated aqueous NH4Cl solution, extracted with AcOEt, and washed with brine. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. The recidue was purified by chromatography on silica-gel with 70% AcOEt/hexane to give 642 mg (75%) of 4-[9-(t-butyldimethylsilyloxy)nonyl]-4-hydroxy-7-methoxy-3-methyl-3-(3-pyridyl)chroman.

Workup

  1. stirringstirred for 1 h at room temperature
  2. additionwas added
  3. stirringThe resulting solution was stirred at −78° C. for 30 minutes
  4. stirringstirred for 1 h at room temperature
  5. temperaturecooling
  6. extractionextracted with AcOEt
  7. washwashed with brine
  8. dry with materialThe organic layer was dried over Na2SO4
  9. customthe solvent was removed under reduced pressure
  10. customThe recidue was purified by chromatography on silica-gel with 70% AcOEt/hexane

Sources & evidence

ORD record
ord-f5535ef36f8a41b7b00ca4f5d150d61a
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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