3-Fluoro-4-nitrobenzaldehyde → (E)-3-(3-Fluoro-4-nitro-phenyl)-acrylic acid tert-butyl ester

HRID 1678688ノート

反応式

HRID 1678688 の反応式
CC([O-])(C)C.[K+].[Br-].[C:8]([O:12][C:13]([C:15]1C=CC=CC=1[P+](C)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[F:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][C:43]=1[N+:44]([O-:46])=[O:45])[CH:39]=O>O1CCCC1>[C:8]([O:12][C:13](=[O:14])/[CH:15]=[CH:39]/[C:38]1[CH:41]=[CH:42][C:43]([N+:44]([O-:46])=[O:45])=[C:36]([F:35])[CH:37]=1)([CH3:11])([CH3:10])[CH3:9]

参加物

5

反応物 3

HCID 38081203-Fluoro-4-nitrobenzaldehydeHCID 23665647Potassium tert-butoxideHCID 86640286Tert-butoxy carbonyl methyl triphenyl phosphonium bromide

生成物 1

HCID 66905416(E)-3-(3-Fluoro-4-nitro-phenyl)-acrylic acid tert-butyl ester収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Potassium tert-butylate (0.438 g, 3.9 mmol) was added to a suspension of tert-butoxy carbonyl methyl triphenyl phosphonium bromide (1.61 g, 3.9 mmol; CAS Reg. No. 35000-37-4) in tetrahydrofuran (10 ml). The suspension was stirred for 15 min at ambient temperature. 3-Fluoro-4-nitrobenzaldehyde (600 mg, 3.5 mmol; CAS Reg. No. 160538-51-2) was added, the mixture was stirred for 1.5 h at ambient temperature, poured onto water and extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. The solid was filtered off and the filtrate was concentrated under reduced pressure to give a brown oil which was purified by column chromatography on silica gel using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane:methyl tert-butyl ether (100:0 to 80:20 v/v) to afford the title compound as a brown oil (812 mg, 3.04 mmol; 86%).

後処理

  1. addition160538-51-2) was added
  2. stirringthe mixture was stirred for 1.5 h at ambient temperature
  3. additionpoured onto water
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe solid was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customto give a brown oil which
  10. customwas purified by column chromatography on silica gel using an MPLC system (CombiFlash Companion, Isco Inc.)
  11. washeluting with a gradient of heptane:methyl tert-butyl ether (100:0 to 80:20 v/v)

出典と根拠

ORDレコード
ord-68bd1c32871d4fd0a369144c0ca504bd
出典データセット
uspto-grants-2011_08
特許番号
US08008505B2

反応ノート

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