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

HRID 1690562

반응식

HRID 1690562 반응식
[Cl-].[C:2]([O:6][C:7]([CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[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:2]([O:6][C:7](=[O:8])/[CH:9]=[CH:39]/[C:38]1[CH:41]=[CH:42][C:43]([N+:44]([O-:46])=[O:45])=[C:36]([F:35])[CH:37]=1)([CH3:5])([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 38081203-Fluoro-4-nitrobenzaldehydeHCID 16211488(2-(tert-Butoxy)-2-oxoethyl)triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of (tert-butoxycarbonylmethyl)triphenylphosphonium chloride (1.6 g, 3.9 mmol; [35000-37-4]) in tetrahydrofuran (10 ml) was added potassium tert-butoxide (0.44 g, 3.9 mmol). After stirring for 15 min 3-fluoro-4-nitrobenzaldehyde (0.60 g, 3.5 mmol; [160538-51-2]) was added. After 1.5 h the suspension was poured on water, the phases were separated and the aqueous phase extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash-chromatography using a gradient of n-heptane:tert-butyl methyl ether (100:0 to 80:20) to give the title compound (804 mg, 3.01 mmol; 86%) as light brown solid. MS: m/e=194.0 [M−C4H9O+].

후처리

  1. additionwas added
  2. additionAfter 1.5 h the suspension was poured on water
  3. customthe phases were separated
  4. extractionthe aqueous phase extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash-chromatography

출처 및 근거

ORD 기록
ord-1842b8fe0572404eb61514a4d6062641
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153663B2

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