3,4-dihydro-2H-pyran → HCID 13836887, compound

HRID 609729Notes

Reaction equation

HRID 609729 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Li]C(C)(C)C.[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15]>C1COCC1.O>[CH2:21]([Sn:16]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:17][CH2:18][CH2:19][CH3:20])[CH:6]1[CH2:5][CH2:4][CH:3]=[CH:2][O:1]1)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 15096Tributyltin ChlorideHCID 178418306HCID 178418306, compound

Product 1

HCID 13836887HCID 13836887, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,3-dihydropyran (2.0 g, 23.8 mmol) in dry THF (50 mL) was added tert-BuLi (26.2 mmol) at -78° C. and the resulting solution was stirred at 0° C. for 1 hour. The mixture was cooled to -78° C. and tributylstannyl chloride (5.53 g, 17.0 mmol) was added and stirring was continued for fifteen minutes at which time the reaction mixture was diluted with water and extracted 3× with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The crude product was filtered through a plug of silica gel to yield 5.23 g (59%) of the title compound as a clear liquid.

Workup

  1. temperatureThe mixture was cooled to -78° C.
  2. stirringstirring
  3. waitwas continued for fifteen minutes at which time
  4. extractionextracted 3× with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationThe crude product was filtered through a plug of silica gel

Sources & evidence

ORD record
ord-59573bf268d44806b2d21e08187cc694
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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