Potassium Fluoride → Methyl 4-cyclopropyl-3-(2-fluoro-3-hydroxyphenyl)butanoate

HRID 1662554ノート

反応式

HRID 1662554 の反応式
[Si]([O:8][C:9]1[C:10]([F:25])=[C:11]([C:15]([CH2:21][CH:22]2[CH2:24][CH2:23]2)=[CH:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][CH:14]=1)(C(C)(C)C)(C)C.[Mg].[F-].[K+]>CO>[CH:22]1([CH2:21][CH:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[C:10]=2[F:25])[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:23][CH2:24]1

参加物

5

反応物 3

HCID 522689Potassium FluorideHCID 5462224MagnesiumHCID 67429099Methyl 3-(3-(tert-butyldimethylsilyloxy)-2-fluorophenyl)-4-cyclopropylbut-2-enoate

生成物 1

HCID 57706932Methyl 4-cyclopropyl-3-(2-fluoro-3-hydroxyphenyl)butanoate収率 79%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A 250 mL round bottom flask was charged with 84.D (4.95 g, 13.6 mmol) and MeOH (60 mL) and flushed with N2. To the solution were added magnesium turnings (0.990 g, 40.7 mmol) in one portion (a few turnings were fractured by hammering prior to addition to expose clean metallic edges). The gently bubbling mixture was stirred overnight at room temperature. To the mixture was added potassium fluoride (0.789 g, 13.6 mmol). The resulting mixture was stirred for 1 hour, quenched with 1 N HCl (90 mL), and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (2×50 mL) and brine (1×50 mL), dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 84.E (2.70 g, 79% yield) as a yellow oil.

後処理

  1. customflushed with N2
  2. additionto addition
  3. customThe gently bubbling mixture
  4. stirringThe resulting mixture was stirred for 1 hour
  5. customquenched with 1 N HCl (90 mL)
  6. extractionextracted with EtOAc (2×50 mL)
  7. washThe combined organic layers were washed with water (2×50 mL) and brine (1×50 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

出典と根拠

ORDレコード
ord-52e1b91e38154e8682bf59e785ec876a
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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