Sodium hydride → (E)-4-(4-methoxyphenyl)but-3-enoic acid

HRID 445819

반응식

HRID 445819 반응식
[Br-].[C:2]([CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1.[H-].[Na+]>CS(C)=O.O1CCCC1>[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31](/[CH:32]=[CH:6]/[CH2:5][C:2]([OH:4])=[O:3])=[CH:30][CH:29]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 312444-MethoxybenzaldehydeHCID 2733850(2-Carboxyethyl)triphenylphosphonium bromide

생성물 1

HCID 14713049(E)-4-(4-methoxyphenyl)but-3-enoic acid수율 55.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

The mixture of (2-carboxyethyl)triphenylphosphonium bromide (20.0 g, 54.0 mmol) and 4-methoxybenzaldehyde (6.5 g, 53.5 mmol) in anhydrous DMSO (64 mL) was added slowly to the suspension of 60% NaH in mineral oil (4.3 g, 107 mmol) in anhydrous tetrahydrofuran (32 mL). The reaction mixture was stirred at 0° C. for 30 minutes then warmed to room temperature over 4 hours. The reaction mixture was quenched with 1N HCl (150 mL) and extracted with ethyl acetate. The organic phase was washed with water, brine, dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (50% EtOAc in hexanes) to provide (E)-4-(4-methoxyphenyl)but-3-enoic acid (557) (5.7 g, 55.0%) as a yellow solid.

후처리

  1. temperaturethen warmed to room temperature over 4 hours
  2. customThe reaction mixture was quenched with 1N HCl (150 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-acebfbeec9024465921b93a880490b57
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476308B2

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