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Tetrahydrofuran → (1S,5R,6R)-6-[(E)-3-Oxo-4-phenoxy-1-butenyl]-2-oxabicyclo[3,3,0]octan-3-one

HRID 1701175
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HRID 1701175 반응식
C([C@H]1CC[C@H]2[C@@H]1CC(=O)O2)=O.O1CCCC1.[Li].[O:18]=[C:19]([CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)/[CH:20]=[CH:21]/[C@H:22]1[C@H:29](OC(=O)C2C=CC=CC=2)[CH2:28][C@H:27]2[C@@H:23]1[CH2:24][C:25](=[O:39])[O:26]2>C(O)(=O)C>[O:18]=[C:19]([CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)/[CH:20]=[CH:21]/[C@H:22]1[CH2:29][CH2:28][C@H:27]2[C@@H:23]1[CH2:24][C:25](=[O:39])[O:26]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 3028194LithiumHCID 12767308(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 12884327(1S,5R,6S)-6-formyl-2-oxabicyclo[3,3,0]octan-3-one

생성물 1

HCID 22810300(1S,5R,6R)-6-[(E)-3-Oxo-4-phenoxy-1-butenyl]-2-oxabicyclo[3,3,0]octan-3-one

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of 7.06 g. of (1S,5R,6S)-6-formyl-2-oxabicyclo[3,3,0]octan-3-one [E.J. Corey et al., J. Org. Chem. 39: 256 (1974)] in 450 ml. of absolute tetrahydrofuran is combined with 13.3 g. of the lithium salt of dimethyl-2-oxo-3-phenoxypropyl phosphonate (preparation: see Example 1). The mixture is stirred at room temperature under argon for 2 hours, then neutralized with glacial acetic acid, concentrated under vacuum, combined with 300 ml. of methylene chloride, and the mixture is extracted with 30 ml. of 5% sodium bicarbonate solution and then twice with respectively 30 ml. of water, dried with magnesium sulfate, and evaporated under vacuum. Recrystallization of the residue from isopropanol yields 11.0 g. (84.5% of theory) of the title compound in the form of colorless crystals.

후처리

  1. concentrationconcentrated under vacuum
  2. extractionof methylene chloride, and the mixture is extracted with 30 ml
  3. dry with materialof water, dried with magnesium sulfate
  4. customevaporated under vacuum
  5. customRecrystallization of the residue from isopropanol
  6. customyields 11.0 g

출처 및 근거

ORD 기록
ord-f735cb29878546d99a5c72a4896f6852
출처 데이터셋
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04191823

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