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Water → (3aR,4R,5R,6aS)-4-((E)-4,4-Difluoro-3-oxooct-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

HRID 1874108
Notes
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Reaction equation

HRID 1874108 reaction equation
COP([CH2:7][C:8](=[O:16])[C:9]([F:15])([F:14])[CH2:10][CH2:11][CH2:12][CH3:13])(=O)OC.[H-].[Li+].[O:19]=[C:20]1[O:24][C@H:23]2[CH2:25][C@@H:26]([O:30][C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:32])[C@H:27]([CH:28]=O)[C@H:22]2[CH2:21]1.O>COC(C)(C)C>[F:15][C:9]([F:14])([CH2:10][CH2:11][CH2:12][CH3:13])[C:8](=[O:16])/[CH:7]=[CH:28]/[C@@H:27]1[C@@H:22]2[C@@H:23]([O:24][C:20](=[O:19])[CH2:21]2)[CH2:25][C@H:26]1[O:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 62714Lithium hydrideHCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 11118722Dimethyl (3,3-difluoro-2-oxoheptyl)phosphonate

Product 1

HCID 68482600(3aR,4R,5R,6aS)-4-((E)-4,4-Difluoro-3-oxooct-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateYield 4.8%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of dimethyl (3,3-difluoro-2-oxoheptyl)phosphonate (1) (0.969 g, 3.75 mmol) in anhydrous t-butyl methyl ether (15 ml), lithium hydride (28.6 mg, 3.60 mmol) was added and the mixture was stirred for two hours at room temperature. (3aR,4R,5R,6aS)-2-oxo-5-phenyl carbonyloxyhexahydrocyclopenta[b]furan-4-carbaldehyde (10) (0.686 g, 2.50 mmol) was added thereto and the mixed solution was stirred for approximately 6 hours at room temperature. Water was added to the solution and the mixture was stirred, let to stand and then separated into two layers. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, sequentially washed with 3% aqueous sodium chloride and saturated aqueous sodium chloride, and then dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (Fuji Silysia BW-300SP: 28 g; ethyl acetate:hexane=1:2) to give (3aR,4R,5R,6aS)-4-((E)-4,4-difluoro-3-oxo-1-octenyl)-2-oxo-5-phenylcarbonyloxyhexahydrocyclopenta[b]furan (11) (48.5 mg; 0.119 mmol; yield: 4.8%).

Workup

  1. stirringthe mixed solution was stirred for approximately 6 hours at room temperature
  2. stirringthe mixture was stirred
  3. customseparated into two layers
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washsequentially washed with 3% aqueous sodium chloride and saturated aqueous sodium chloride
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (Fuji Silysia BW-300SP: 28 g; ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-e29c23d1eeff46b39c5d0bad2a36afb5
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08304562B2

Reaction notes

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