3,4-dihydro-2H-pyran → HCID 18624687, compound

HRID 637807Notes

Reaction equation

HRID 637807 reaction equation
O1C=CCCC1.[Na].O.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12](S(O)(=O)=O)=[CH:11]C=1.[C:20](=[O:23])(O)[O-:21].[Na+]>C(Cl)Cl>[O:21]1[C:20](=[O:23])[CH:19]=[C:9]2[CH:11]=[CH:12][CH:13]=[C:14]12

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 5360545Sodium

Product 1

HCID 18624687HCID 18624687, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

571.5 mg (1.82 mmol) of [3S-[3S-[3α,3aα,4α(1E,3R*),5β,6aα]]-hexahydro-3-fluoro-5-hydroxy-4-(3-hydroxy-4,4-dimethyl-1-octenyl)-2H-cyclopenta[b]furan-2-one was dissolved in 20 ml of methylene chloride (freshly filtered through aluminum oxide, activity I) under a positive argon pressure. 2.0 ml (21.9 mmol) of dihydropyran (freshly dist. from sodium) was added under stirring followed by a crystal of p-toluenesulfonic acid monohydrate (9.7 mg; 0.05 mmol). The mixture was stirred at room temperature for 30 min, poured into 50 ml of sat. aqueous sodium bicarbonate and extracted three times with 30 ml of methylene chloride. The extracts were washed twice with 50 ml of brine, combined, dried over MgSO4 and concentrated at reduced pressure. The crude product (1.14 g, oil) was chromatographed on a 100 g silica gel column with ether/petroleum ether (1:1) yielding 797 mg (1.65 mmol)91% of [3S-[3α,3aα,4α(1E,3R*),-5β,6aα]]-hexahydro-3-fluoro-5-[(tetrahydro-2H-pyran-2-yl)oxy]-4-[3-(tetrahydro-2H-pyran-2-yl)oxy]-4,4-dimethyl-1-octenyl]-2H-cyclopenta[b]furan-2-one as a clear oil(mixture of THP-diastereomers). [α]D25 -32.46° in CHCl3, c=0.8780.

Workup

  1. filtrationfreshly filtered through aluminum oxide, activity I) under a positive argon pressure
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. extractionextracted three times with 30 ml of methylene chloride
  4. washThe extracts were washed twice with 50 ml of brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated at reduced pressure
  7. customThe crude product (1.14 g, oil) was chromatographed on a 100 g silica gel column with ether/petroleum ether (1:1)

Sources & evidence

ORD record
ord-9a9a88845abe4e148d0a3a917851ab65
Source dataset
uspto-grants-1985_12
Patent number
US04558142

Reaction notes

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