Water → (2-Benzyloxyphenyl)-(4-methylsulfanyl-phenyl)methanol

HRID 554505ノート

反応式

HRID 554505 の反応式
CCCCCC.C([Li])CCC.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:27][S:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[O:34])=[CH:31][CH:30]=1.O>C1COCC1>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:33]([C:32]1[CH:35]=[CH:36][C:29]([S:28][CH3:27])=[CH:30][CH:31]=1)[OH:34])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 769854-(Methylthio)benzaldehydeHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 178418244HCID 178418244、化合物

生成物 1

HCID 67459728(2-Benzyloxyphenyl)-(4-methylsulfanyl-phenyl)methanol収率 58%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 6.92 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (2.89 g, 11.0 mmol) in THF (38 mL) at −78° C. and the mixture solution was stirred at the same temperature for 30 minutes. To this solution, a solution of 4-methylsulfanylbenzaldehyde (1.67 g, 11.0 mmol) in THF (12 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for one hour, and then water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (2.14 g, 58%).

後処理

  1. stirringThe reaction mixture was stirred at the same temperature for one hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

出典と根拠

ORDレコード
ord-becdbd9e16964f3abdd2d43f65bd4051
出典データセット
uspto-grants-2011_11
特許番号
US08048897B2

反応ノート

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