HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate → (1S,5R,6R,7R)-6-[(E)-3-Oxo-3-({2RS}-1,3-benzodioxan-2-yl)-1-propenyl]-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one

HRID 1856056
Notes
Print preview

Reaction equation

HRID 1856056 reaction equation
[CH:1]([C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2)=O.[O:21]=[C:22]([CH:43]1[O:48][C:47]2[CH:49]=[CH:50][CH:51]=[CH:52][C:46]=2[CH2:45][O:44]1)[CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1C=CC=CC=1>[O:21]=[C:22]([CH:43]1[O:48][C:47]2[CH:49]=[CH:50][CH:51]=[CH:52][C:46]=2[CH2:45][O:44]1)/[CH:23]=[CH:1]/[C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 233474421-(2H,4H-1,3-Benzodioxin-2-yl)-2-(triphenyl-lambda~5~-phosphanylidene)ethan-1-one

Product 1

HCID 70588948(1S,5R,6R,7R)-6-[(E)-3-Oxo-3-({2RS}-1,3-benzodioxan-2-yl)-1-propenyl]-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Under an argon atmosphere, 7 g. of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one, E. J. Corey et al., J. Amer. Chem. Soc. 91, 5675 (1969), and 11.2 g. of [2-oxo-2-(1,3-benzodioxan-2-yl)-ethylidene]-triphenylphosphorane were agitated at room temperature for 16 hours in 300 ml. of benzene. The reaction mixture was then evaporated to dryness under vacuum. The residue was purified by column chromatography on silica gel with hexane/20-60% ethyl acetate as the eluent. Yield: 5 g. of an oil.

Workup

  1. customThe reaction mixture was then evaporated to dryness under vacuum
  2. customThe residue was purified by column chromatography on silica gel with hexane/20-60% ethyl acetate as the eluent

Sources & evidence

ORD record
ord-9f1fb030ac5c435496645533e7892150
Source dataset
uspto-grants-1980_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04217360

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes