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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
Notes
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Reaction equation

HRID 1701175 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f735cb29878546d99a5c72a4896f6852
Source dataset
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04191823

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes