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Diisopropylamine → 4-Pyridyl-t-butydimethylsilyloxymethyl 4-t-butylphenyl ketone

HRID 1418052
Notes
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Reaction equation

HRID 1418052 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.F[C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH:22]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])=[O:21])=[CH:16][CH:15]=1.[C:37](C1C=CC(C(N(OC)C)=O)=CC=1)([CH3:40])([CH3:39])[CH3:38]>C1COCC1>[C:37]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH:22]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[O:23][Si:24]([C:27]([CH3:29])([CH3:30])[CH3:28])([CH3:25])[CH3:26])=[O:21])=[CH:16][CH:15]=1)([CH3:40])([CH3:39])[CH3:38]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 29870884-(tert-Butyl)-N-methoxy-N-methylbenzamideHCID 10991586HCID 10991586, compoundHCID 178418339Butyllithium

Product 1

HCID 674868814-Pyridyl-t-butydimethylsilyloxymethyl 4-t-butylphenyl ketoneYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Conditions

Temperature
-20 °C

Procedure

To a cooled solution of diisopropylamine (183 mg, 1.81 mmol) in dry THF (0.35 mL) at -20° C. was added a solution of n-butyllithium in hexanes (0.83 mL of a 2.5M solution, 2.08 mmol). Stirred at -20° C. for 1 hr and then added a solution of 4-pyridyl-t-butydimethylsilyloxymethyl 4-fluorophenyl ketone from Step B (383 mg, 1.72 mmol) in THF (0.45 mL). Stirred at -20° C. for 45 min, resulting in a thick yellow-brown solution. A solution of 4-t-butyl-N-methoxy-N-methyl-benzamide (400 mg, 1.81 mmol) in THF (0.5 mL) was added and the solution stirred at -20° to 0° C. for 5 h. The reaction was cooled to -20° C. and quenched by the addition of a saturated ammonium chloride solution. The reaction mixture was then extracted with ethyl acetate (3 times) and the combined extracts washed successively with water (2 times) and saturated salt solution and dried over anhydrous sodium sulfate. The mixture was filtered and the solvent removed by rotoevaporation. The residue was purified by flash column chromatography on silica gel eluted with 5-10% ethyl acetate in hexanes to yield the title compound as a yellow oil (341 mg, 49% yield).

Workup

  1. stirringStirred at -20° C. for 45 min
  2. customresulting in a thick yellow-brown solution
  3. stirringthe solution stirred at -20° to 0° C. for 5 h
  4. temperatureThe reaction was cooled to -20° C.
  5. customquenched by the addition of a saturated ammonium chloride solution
  6. extractionThe reaction mixture was then extracted with ethyl acetate (3 times)
  7. washthe combined extracts washed successively with water (2 times) and saturated salt solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationThe mixture was filtered
  10. customthe solvent removed by rotoevaporation
  11. customThe residue was purified by flash column chromatography on silica gel
  12. washeluted with 5-10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-73b6e390f88c4898a771f7b3b746d191
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05880139

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes