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

HRID 227620

反応式

HRID 227620 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 241Benzene溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-398a5d3424134113a4bd29f8ff47bc12
出典データセット
uspto-grants-2009_07
特許番号
US07560552B2

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