Butyl iodide → HCID 19010813、化合物

HRID 1741837ノート

反応式

HRID 1741837 の反応式
I[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:6][O:7][C:8]1[CH:16]=[C:15]([CH:17]=[C:18]([CH3:20])[CH3:19])[CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11]>C1C=CC=CC=1.CN(C)C=O.[Cu].[Zn].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>[CH3:6][O:7][C:8]1[CH:16]=[C:15]([CH:17]=[C:18]([CH3:20])[CH3:19])[CH:14]=[CH:13][C:9]=1[C:10](=[O:11])[CH2:2][CH2:3][CH2:4][CH3:5]

参加物

7

反応物 2

HCID 10962Butyl iodideHCID 190108112-Methoxy-4-(2-methyl-1-propen-1-yl)benzoyl chloride

生成物 1

HCID 19010813HCID 19010813、化合物収率 60.1%

試薬・触媒・溶媒 4

HCID 10290809Zinc copper couple触媒HCID 178418397HCID 178418397、化合物触媒HCID 241Benzene溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 1-iodobutane (185 mg) and zinc-copper couple (101 mg) in benzene (3 ml) and N,N-dimethylformamide (0.2 ml) was stirred at 60° C. for 2 hours. To the mixture, a solution of tetrakis(triphenylphosphine)palladium (31 mg) and 2-methoxy-4-(2-methyl-1-propenyl)benzoyl chloride (prepared from 138 mg of 2-methoxy-4-(2-methyl-1propenyl)benzoic acid and 0.07 ml of oxalyl chloride) in benzene (2 ml) was added, and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and the organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (9:1) to give 2'-methoxy-4'-(2-methyl-1-propenyl)valerophenone (91 mg) 10 as an oil.

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel column
  9. washeluting with a mixture of hexane and ethyl acetate (9:1)

出典と根拠

ORDレコード
ord-083f3233553d4dbfa3c7d233603f8751
出典データセット
uspto-grants-1994_08
特許番号
US05334716

反応ノート

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