Diethyl (cyanomethyl)phosphonate → HCID 66823993, 화합물

HRID 1692933

반응식

HRID 1692933 반응식
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].O=[C:19]1[CH2:22][C:21]([C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:20]1>O1CCCC1>[C:7]([CH:9]=[C:19]1[CH2:22][C:21]([C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:20]1)#[N:8]

참가 물질

5

반응물 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 49133571,1-Bis(propan-2-yl) 3-oxocyclobutane-1,1-dicarboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 66823993HCID 66823993, 화합물수율 90.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a mixture of 1.0000 M of potassium tert-butoxide in tetrahydrofuran (17 mL) and THF (10 mL) was added dropwise, at 0° C., diethyl cyanomethylphosphonate (2.7 mL, 0.017 mol). The reaction was warmed to rt and 30 min later cooled to 0° C. again. To the reaction mixture was added a solution of diisopropyl 3-oxocyclobutane-1,1-dicarboxylate (2.7 g, 0.011 mol) in THF (10 mL). The reaction was allowed to warm up to rt gradually and stirred at rt for 2 h. The reaction was quenched with saturated aq. NH4Cl and the organic solvent was reduced. The mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, concentrated and purified with Combiflash (silica gel, 0-35% EtOAc/Hex) to give the desired product (2.65 g) as light yellow oil.

후처리

  1. additionwas added dropwise, at 0° C.
  2. temperaturelater cooled to 0° C. again
  3. temperatureto warm up to rt gradually
  4. customThe reaction was quenched with saturated aq. NH4Cl
  5. extractionThe mixture was extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. custompurified with Combiflash (silica gel, 0-35% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-f81beaf1aaf14676b664d6b9fc5ec6d6
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158616B2

연결된 노트

불러오는 중…