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3,4-dihydro-2H-pyran → HCID 117874872, compound

HRID 517369
Notes
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Reaction equation

HRID 517369 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[O:6][CH2:7][C@H:8]([OH:21])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:18]2[C@@H:14]([O:15][C:16](=[O:19])[CH2:17]2)[CH2:13][C@H:12]1[OH:20].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.[C:33](=[O:36])(O)[O-].[Na+]>C1COCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]1[O:20][C@@H:12]1[CH2:13][C@@H:14]2[O:15][C:16](=[O:19])[CH2:17][C@@H:18]2[C@H:11]1/[CH:10]=[CH:9]/[C@@H:8]([O:21][CH:23]1[CH2:24][CH2:3][CH2:2][CH2:33][O:36]1)[CH2:7][O:6][C:5]1[CH:22]=[CH:23][CH:24]=[C:3]([C:2]([F:25])([F:1])[F:26])[CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 12042328(+)-(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one

Product 1

HCID 117874872HCID 117874872, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 521998
p-Toluenesulfonic acid monohydrate
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.35 g, 1.8 mmol) was added to a solution of (3aR,4R,5R,6aS)-4-((R,E)-4-(3-(trifluoromethyl)phenoxy)-3-hydroxybut-1-enyl)-hexahydro-5-hydroxycyclopenta[b]furan-2-one (15.0 g, 40.3 mmol) and 3,4-dihydro-2H-pyran (8.47 g, 100.7 mmol) in THF (200 mL) at room temperature and the mixture was stirred for 2.5 hr (TLC monitoring). Saturated aqueous solution of sodium bicarbonate (200 mL) was poured into the reaction mixture and the mixture was stirred for 5 minutes. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 mL). The combined organic layers were dried over magnesium sulfate, filtered off solid and concentrated under reduced pressure to give 24.0 g of crude product. The crude product was purified by column chromatography and then concentrated under reduced pressure to provide 19.0 g of the titled compound (87.5% yield).

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (200 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered off solid
  6. concentrationconcentrated under reduced pressure
  7. customto give 24.0 g of crude product
  8. customThe crude product was purified by column chromatography
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c7c69a790fd4f928c2b87e59a89d547
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115109B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes