Chloroiodomethane → 2-(2-(Trifluoromethyl)phenyl)oxirane

HRID 2062

反応式

HRID 2062 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]([CH:9]=[O:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.I[CH2:14]Cl.C[Li]>O1CCCC1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][O:10]1

参加物

5

反応物 3

HCID 11644ChloroiodomethaneHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 178418348HCID 178418348、化合物

生成物 1

HCID 139032672-(2-(Trifluoromethyl)phenyl)oxirane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

α,α,α-trifluoro-o-tolualdehyde (3 g) was dissolved in anhydrous tetrahydrofuran and cooled to -78° C., iodochloromethane (1.38 ml) was then added, followed by methyllithium (1.5M complexed with lithium bromide) (12 ml) added over 5 minutes. The reaction was left to warm up to room temperature overnight. The reaction was quenched using saturated ammonium chloride solution and extracted using diethyl ether (2×50 ml). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to afford a brown oil. Purification on flash silica eluted with 100% hexane up to 5% EtOAC in hexane afforded a colourless oil (1.1 g). 1H NMR (250 MHz, CDCl3) δ2.61-2.71 (1H, dd), 3.14-3.25 (1H, dd), 4.17-4.27 (1H, m), 7.33-7.70 (5H, m).

後処理

  1. additionadded over 5 minutes
  2. waitThe reaction was left
  3. temperatureto warm up to room temperature overnight
  4. customThe reaction was quenched
  5. extractionextracted
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto afford a brown oil
  10. customPurification on flash silica
  11. washeluted with 100% hexane up to 5% EtOAC in hexane

出典と根拠

ORDレコード
ord-622fcecd2a0b4607a07fac649d6051df
出典データセット
uspto-grants-1998_03
特許番号
US05728695

関連ノート

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