4-(4-Bromophenoxy)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonate → 3-(2-(4-Bromophenoxy)ethyl)oxetane

HRID 338532ノート

反応式

HRID 338532 の反応式
CC1C=CC(S(O[CH2:12][CH:13]([CH2:24][OH:25])[CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)(=O)=O)=CC=1.C([Li])CCC>O1CCCC1>[Br:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH2:14][CH:13]2[CH2:12][O:25][CH2:24]2)=[CH:22][CH:21]=1

参加物

4

反応物 2

HCID 866988534-(4-Bromophenoxy)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonateHCID 178418339Butyllithium2 回

生成物 1

HCID 847090473-(2-(4-Bromophenoxy)ethyl)oxetane収率 37.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(4-bromophenoxy)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonate (0.450 g, 1.04 mmol) in anhydrous tetrahydrofuran (10 mL) was added n-butyl lithium (0.42 mL, 2.5M, 1.04 mmol) dropwise at 0° C. After complete addition of the n-butyl lithium solution, the resulting mixture was heated at reflux overnight. The reaction was carefully quenched with water and extracted with ethyl acetate (5×20 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by flash chromatography (0-20% ethyl acetate/petroleum ether) to afford the title compound (0.10 g, 37%) as a white solid. 1H NMR (400 MHz, CDCl3) ppm 7.37 (d, 2H), 6.74 (d, 2H), 4.89-4.78 (m, 2H), 4.56-4.45 (m, 2H), 3.94-3.87 (m, 2H), 3.30-3.17 (m, 1H), 2.23-2.12 (m, 2H)

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customThe reaction was carefully quenched with water
  4. extractionextracted with ethyl acetate (5×20 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product
  9. customThe crude product was purified by flash chromatography (0-20% ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-745365aebfc64907bce6143b9c854901
出典データセット
uspto-grants-2014_11
特許番号
US08889730B2

反応ノート

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