Sodium hydride → Tert-butyl 3-(4-cyanophenyl)prop-2-enoate

HRID 880398노트

반응식

HRID 880398 반응식
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(OCC)=O)C.[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1)#[N:20]>C1COCC1.CC(OC)(C)C.[NH4+].[Cl-]>[C:19]([C:21]1[CH:28]=[CH:27][C:24](/[CH:25]=[CH:11]/[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:23][CH:22]=1)#[N:20]

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 660424-CyanobenzaldehydeHCID 2773685tert-Butyl diethylphosphonoacetate

생성물 1

HCID 11287649Tert-butyl 3-(4-cyanophenyl)prop-2-enoate수율 101.3%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매3회HCID 15413tert-Butyl methyl ether용매HCID 25517Ammonium Chloride용매

실험 절차

A flame dried three-neck round-bottom flask equipped with a magnetic stirring bar, a thermometer, an addition funnel and a nitrogen inlet was charged with NaH (3.96 g, 94.7 mmol) and anhydrous THF (120 mL). Tert-butyl diethylphosphonoacetate (23.2 mL, 94.7 mmol) dissolved in anhydrous THF (20 mL) was added dropwise via the addition funnel over a period of 30 min. After the completion of addition, the reaction mixture was stirred at rt for another 30 min. A solution of 4-cyanobenzaldehyde (11.3 g, 86.1 mmol) dissolved in anhydrous THF (20 mL) was added to the reaction mixture dropwise via the addition funnel over a period of 30 min. After the end of the addition, the reaction mixture was stirred at rt for 1 h, then diluted with MTBE (200 mL) and sat. NH4Cl (150 mL). The organic layer was separated, washed with 25 mL of water and 25 mL of sat. NH4Cl, dried over MgSO4, filtered and evaporated to dryness to give 20.0 g title compound as a solid (100%). 1H NMR (400 MHz, CDCl3) δ ppm 1.56 (s, 9H) 6.47 (d, J=16 Hz, 1H) 7.58 (d, J=16 Hz, 1H) 7.61 (d, J=8 Hz, 2H) 7.68 (d, J=8 Hz, 2H).

후처리

  1. customA flame dried three-neck round-bottom flask
  2. customequipped with a magnetic stirring bar
  3. additionwas added dropwise via the addition funnel over a period of 30 min
  4. additionAfter the completion of addition
  5. additionwas added to the reaction mixture dropwise via the addition funnel over a period of 30 min
  6. additionAfter the end of the addition
  7. stirringthe reaction mixture was stirred at rt for 1 h
  8. customThe organic layer was separated
  9. washwashed with 25 mL of water and 25 mL of sat. NH4Cl
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated to dryness

출처 및 근거

ORD 기록
ord-7bdebeabf5c643fd910f2f7b5bf5d3e0
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993577B2

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