4-Methyloxybenzyl chloride → HCID 23028716、化合物

HRID 748709ノート

反応式

HRID 748709 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Na+].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 699934-Methyloxybenzyl chlorideHCID 23664783Sodium 4-chlorobenzenesulfinate

生成物 1

HCID 23028716HCID 23028716、化合物

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 2631-Butanol溶媒

反応条件

温度
70 °C

実験手順

A butanol (5 ml) suspension of sodium 4-chlorobenzenesulfinate (264 mg, 1.33 mmol), 4-methoxybenzyl chloride (181 μl, 1.33 mmol) and tetrabutylammonium bromide (24 mg) was stirred at 70° C. for 3 days. After cooling the reaction mixture to room temperature, the solvent was concentrated under reduced pressure. Ethyl acetate was added to the residue and the mixture was washed successively with water and brine, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate (=5:1) eluate was concentrated under reduced pressure, whereby the title compound (90 mg, 23%) was obtained as a white solid.

後処理

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. washthe mixture was washed successively with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe fraction obtained from the hexane
  9. concentrationethyl acetate (=5:1) eluate was concentrated under reduced pressure, whereby the title compound (90 mg, 23%)
  10. customwas obtained as a white solid

出典と根拠

ORDレコード
ord-4a92ae40b09643fb9b0c55590b69120a
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

反応ノート

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