1,5-Dibromopentane → 1-[2-[(5-Bromopentyl)oxy]ethyl]-4-(methylthio)benzene

HRID 568880ノート

反応式

HRID 568880 の反応式
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-].[Na+]>O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

参加物

5

反応物 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 27600862-(4-Methylsulfanylphenyl)ethanol

生成物 1

HCID 200713861-[2-[(5-Bromopentyl)oxy]ethyl]-4-(methylthio)benzene収率 76.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

4-(methylthio)benzeneethanol (7.44 g) and 1,5 dibromopentane (30.48 g) were stirred rapidly at room temperature with TAB (1.0 g) and 12.5M aqueous sodium hydroxide (35 ml) for 64 h. The mixture was diluted with water (170 ml), extracted with ER (3×200 ml), and the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml), dried and evaporated. The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97) to give the title compound as a colourless oil (10.68 g). T.l.c. (ER-CX 1:79) Rf 0.08.

後処理

  1. extractionextracted with ER (3×200 ml)
  2. washthe combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml)
  3. customdried
  4. customevaporated
  5. customThe residual oil (29.29 g) was purified by FCC
  6. washeluting with ER-CX (0:100→3:97)

出典と根拠

ORDレコード
ord-e53995d0ce6f4a9f8753765b5e6ed48c
出典データセット
uspto-grants-1988_03
特許番号
US04730008

反応ノート

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