Sodium hydride → HCID 178468870, 화합물

HRID 1035708노트

반응식

HRID 1035708 반응식
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH:19]([C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]2[CH:37]=[CH:36][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)=O.S([O-])(O)(=O)=O.[K+]>CN(C=O)C>[C:13]([O:12][C:10](/[CH:9]=[CH:19]/[C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]2[CH:28]=[CH:29][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:36][CH:37]=2)[CH2:23][CH2:22]1)=[O:11])([CH3:14])([CH3:15])[CH3:16]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 2773685tert-Butyl diethylphosphonoacetateHCID 178468872HCID 178468872, 화합물

생성물 1

HCID 178468870HCID 178468870, 화합물수율 80.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

0.682 g of tert-butyl diethylphosphonoacetate (2.7 mmol, 1.1 eq.) is placed in 5 mL of DMF at 4° C. with stirring, 0.065 g of sodium hydride (2.7 mmol, 1.1 eq.) is added. After stirring for 1 hour, 0.64 g of ethyl trans-4-(4-formylcyclohexyl)benzoate (2.46 mmol, 1 eq.) dissolved in 5 mL of DMF is added dropwise. After stirring for 18 hours, 10% potassium hydrogen sulfate solution is added. The reaction medium is extracted twice with ethyl acetate. The organic phases are combined, washed twice with water, washed with brine, dried over sodium sulfate and evaporated. The residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 10% to 20%. 0.71 g of ethyl trans-4-[4-((E)-2-tert-butoxycarbonylvinyl)cyclohexyl]benzoate is obtained.

후처리

  1. stirringAfter stirring for 1 hour
  2. additionis added dropwise
  3. stirringAfter stirring for 18 hours
  4. extractionThe reaction medium is extracted twice with ethyl acetate
  5. washwashed twice with water
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 10% to 20%

출처 및 근거

ORD 기록
ord-737ff7aed4df4910bdf67333ac419e00
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546391B2

반응 노트

불러오는 중…