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Ethanol → HCID 10926216, 화합물

HRID 975485
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HRID 975485 반응식
[CH2:1]1CCC(N=C=NC2CCCCC2)C[CH2:2]1.[C:16]([O:20][C:21]([NH:23][CH2:24][P:25]([CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(=[O:27])[OH:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(O)C>C1COCC1>[C:16]([O:20][C:21]([NH:23][CH2:24][P:25]([CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(=[O:26])[O:27][CH2:1][CH3:2])=[O:22])([CH3:19])([CH3:18])[CH3:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 11120883HCID 11120883, 화합물

생성물 1

HCID 10926216HCID 10926216, 화합물수율 34.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

DCC (190 mg, 0.92 mmol) in THF (4 ml) is added dropwise in the course of 4 minutes to a solution of the phosphinic acid 1 (270 mg, 0.83 mmol) in dry THF (4 ml) and abs. ethanol (0.30 ml, 5.15 mmol) which is boiling under reflux. After 1.5 hours (checking by TLC), the reaction solution is cooled to room temperature and filtered. The filter residue is washed with ether. The filtrate is extracted with water (2×20 ml). The organic phase is dried over Na2SO4 and concentrated under reduced pressure. After purification by column chromatography on silica gel (ethyl acetate/heptane=3:2), the phosphinic acid ester 3 (100 mg, 34% of theory) is obtained. M.p. 117.5°-120° C.

후처리

  1. temperatureunder reflux
  2. filtrationfiltered
  3. washThe filter residue is washed with ether
  4. extractionThe filtrate is extracted with water (2×20 ml)
  5. dry with materialThe organic phase is dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customAfter purification by column chromatography on silica gel (ethyl acetate/heptane=3:2)

출처 및 근거

ORD 기록
ord-9d1fc4e457ae408b999b6b820f27140f
출처 데이터셋
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05608098

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