Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-Ethyl 3-cyclobutylacrylate

HRID 1055053ノート

反応式

HRID 1055053 の反応式
C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])C=CC=CC=1.[CH:26]1([CH:30]=O)[CH2:29][CH2:28][CH2:27]1>ClCCl>[CH:26]1(/[CH:30]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:27][CH2:28][CH2:29]1

参加物

4

反応物 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 12431621Cyclobutanecarbaldehyde2 回

生成物 1

HCID 57706492(E)-Ethyl 3-cyclobutylacrylate収率 23%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ethyl 2-triphenylphosphoranylideneacetate (9.32 g, 26.74 mmol) was added to a solution of cyclobutanecarbaldehyde, 45a, (1.50 g, 17.83 mmol) in dichloromethane (30 mL). The reaction mixture was briefly purged with nitrogen and capped allowed to stir at room temperature overnight. All volatiles were removed at reduced pressure and the residue was dissolved in Et2O (100 mL) and hexanes (25 mL). The resulting pink precipitate was filtered off and discarded. The solvent was removed from the filtrate at reduced pressure. The crude product was purified via silica gel chromatography (0-20% EtOAc/Hexanes gradient) to afford 646 mg (23%) of the desired product: 1H NMR (400 MHz, CDCl3) δ 7.05 (dd, J=15.6, 6.8 Hz, 1H), 5.73 (dd, J=15.6, 1.4 Hz, 1H), 4.29-4.09 (m, 2H), 3.20-2.98 (m, 1H), 2.28-2.09 (m, 2H), 2.04-1.78 (m, 4H), 1.36-1.18 (m, 3H).

後処理

  1. customThe reaction mixture was briefly purged with nitrogen
  2. customcapped
  3. customAll volatiles were removed at reduced pressure
  4. dissolutionthe residue was dissolved in Et2O (100 mL)
  5. filtrationThe resulting pink precipitate was filtered off
  6. customThe solvent was removed from the filtrate at reduced pressure
  7. customThe crude product was purified via silica gel chromatography (0-20% EtOAc/Hexanes gradient)

出典と根拠

ORDレコード
ord-318b86236e7641249ab38ed454c9c411
出典データセット
uspto-grants-2016_07
特許番号
US09394302B2

反応ノート

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