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Diethyl Ether → HCID 22821307, 화합물

HRID 67738
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HRID 67738 반응식
C([Li])CCC.C[C:7](C)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:9](=[O:15])[CH2:10]P(=O)([O-])[O-].CCOCC.[CH:28]([C@H:30]1[C@H:37]([O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:36][C@H:35]2[C@@H:31]1[CH2:32][C:33](=[O:47])[O:34]2)=O>CCCCCC.C(O)(=O)C.O1CCCC1>[O:15]=[C:9]([CH2:8][CH2:7][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)/[CH:10]=[CH:28]/[C@H:30]1[C@H:37]([O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:36][C@H:35]2[C@@H:31]1[CH2:32][C:33](=[O:47])[O:34]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 3283Diethyl Ether2회HCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 53442789Dimethyl-2-oxo-4-phenylbutylphosphonateHCID 178418339Butyllithium

생성물 1

HCID 22821307HCID 22821307, 화합물

시약·촉매·용매 3

HCID 176
Acetic Acid
용매
HCID 8028Tetrahydrofuran용매
HCID 8058Hexane용매

실험 절차

At 20° under argon, 20 ml. of a 2-molar butyllithium solution in hexane was added dropwise to a solution of 11.2 g. of dimethyl-2-oxo-4-phenylbutylphosphonate in 400 ml. of ether. The mixture was stirred for 5 minutes and then 600 ml. of ether was added thereto and the mixture again stirred for 5 minutes at 20°. Thereafter, a solution of 9.26 g. of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one [J. Amer. Chem. Soc. 96, 5865 (1974)] in 150 ml. of tetrahydrofuran was added dropwise to this mixture, and the latter was agitated for 30 minutes at 20°. 6 ml. of glacial acetic acid was added thereto, and the mixture was evaporated under vacuum. The residue was taken up in 600 ml. of methylene chloride, shaken twice with respectively 100 ml. of saturated sodium bicarbonate solution, twice with respectively 100 ml. of water, dried over magnesium sulfate, and evaporated under vacuum. After recrystallization from isopropyl ether/methylene chloride, 11 g. of the title compound was obtained as colorless crystals; m.p. 119°-120°.

후처리

  1. customAt 20°
  2. stirringthe mixture again stirred for 5 minutes at 20°
  3. stirringthe latter was agitated for 30 minutes at 20°
  4. customthe mixture was evaporated under vacuum
  5. stirringof methylene chloride, shaken twice with respectively 100 ml
  6. dry with materialof water, dried over magnesium sulfate
  7. customevaporated under vacuum
  8. customAfter recrystallization from isopropyl ether/methylene chloride, 11 g

출처 및 근거

ORD 기록
ord-5b290b7740b4424bbd16e3567573194c
출처 데이터셋
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04346228

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