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4-Nitrobenzoyl chloride → 4-{[Tert-butyl(dimethyl)silyl]oxy}-1-(4-nitrophenyl)butan-1-one

HRID 227620
Notes
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Reaction equation

HRID 227620 reaction equation
[C:1]([Si:5]([O:8][CH2:9][CH2:10][CH2:11]I)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C1C=CC=CC=1.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Si:5]([O:8][CH2:9][CH2:10][CH2:11][C:20]([C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=1)=[O:21])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 11022956Tert-butyl-(3-iodopropoxy)-dimethylsilane

Product 1

HCID 116022464-{[Tert-butyl(dimethyl)silyl]oxy}-1-(4-nitrophenyl)butan-1-oneYield 47.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241
Benzene
Solvent
2×
HCID 6228DimethylformamideSolvent

Procedure

A mixture of Zn—Cu couple (2.68 g, 41.3 mmol) and tert-butyl(3-iodopropoxy)dimethylsilane (8.26 g, 27.5 mmol) in benzene (55 mL) and DMF (3.6 mL) was stirred vigorously at room temperature for 1 hour, heated to 60° C. for 4 hours, cooled to room temperature, and treated with a solution of 4-nitrobenzoyl chloride (3.4 g, 18.3 mmol) and (Ph3P)4Pd (0.847 g, 0.73 mmol) in benzene (36 mL) by cannula. The mixture was stirred for 1 hour, filtered through diatomaceous earth (Celite™), and partitioned between saturated NH4Cl and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate and the combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes to provide 2.81 g of the desired product. MS(ESI(−)) m/e 322 (M−H)−.

Workup

  1. temperatureheated to 60° C. for 4 hours
  2. temperaturecooled to room temperature
  3. stirringThe mixture was stirred for 1 hour
  4. filtrationfiltered through diatomaceous earth (Celite™)
  5. custompartitioned between saturated NH4Cl and ethyl acetate
  6. extractionThe aqueous phase was extracted three times with ethyl acetate
  7. washthe combined extracts were washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-398a5d3424134113a4bd29f8ff47bc12
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560552B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes