3,4-dihydro-2H-pyran → HCID 68734777, compound

HRID 1470682Notes

Reaction equation

HRID 1470682 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[OH:7][C@@H:8]1[CH2:16][C@@H:11]2[O:12][C:13](=[O:15])[CH2:14][C@@H:10]2[C@H:9]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>ClCCl>[CH2:17]([C@@H:9]1[C@@H:10]2[C@@H:11]([O:12][C:13](=[O:15])[CH2:14]2)[CH2:16][C@H:8]1[O:7][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 68735663HCID 68735663, compound

Product 1

HCID 68734777HCID 68734777, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dihydropyran (60 μL, 0.66 mmol) and PPTs (11 mg, 0.045 mmol) were added to a solution of 5-3 (81 mg, 0.32 mmol) in dichloromethane (1.2 mL). After overnight stirring, the reaction was washed with 1 M HCl, saturated NaHCO3 solution and brine. The organic layer was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (100 mg, 93%).

Workup

  1. washthe reaction was washed with 1 M HCl, saturated NaHCO3 solution and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification of the residue by flash chromatography on silica gel (Isco Combiflash unit)

Sources & evidence

ORD record
ord-3bcdacf5b2f84eb18ba9b11624a36a17
Source dataset
uspto-grants-2015_04
Patent number
US09006464B2

Reaction notes

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