Sodium hydride → HCID 22707002, compound

HRID 1696693Notes

Reaction equation

HRID 1696693 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.Cl[Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22].[Cl-].[NH4+]>C(OCC)(=O)C.C1COCC1>[C:12]1([CH2:11][C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[CH:9][CH:8]=2)=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75607Benzyl 4-hydroxyphenyl ketoneHCID 139400Triisopropylsilyl chloride

Product 1

HCID 22707002HCID 22707002, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

With cooling with ice, 60% oily sodium hydride (804 mg) was added to a THF (100 mL) solution of 1-(4-hydroxyphenyl)-2-phenylethanone (4.7 g, 22.1 mmol), and stirred for 10 minutes. With cooling with ice, chlorotriisopropylsilane (5.2 mL) was added to the reaction liquid, and stirred for 2 hours. Aqueous saturated ammonium chloride solution was added to the reaction liquid, then diluted with ethyl acetate and extracted. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1). The obtained crude product was recrystallized from ethanol to obtain the intended compound (3.8 g, 31%).

Workup

  1. additionwas added to the reaction liquid
  2. stirringstirred for 2 hours
  3. extractionextracted
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)
  7. customThe obtained crude product
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-c84616b2b34440328d7baf1f1e828992
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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