Tetrahydrofuran → HCID 70009598, compound

HRID 564340Notes

Reaction equation

HRID 564340 reaction equation
S([O-])(=O)(=O)[CH3:2].[C:6](O[K])(C)([CH3:8])[CH3:7].[CH2:12]1[CH2:16][O:15][CH2:14][CH2:13]1>O>[CH2:8]([CH:14]1[CH:13]=[CH:2][CH:12]=[CH:16][O:15]1)[CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 85257MethanesulfonateHCID 178418922HCID 178418922, compound

Product 1

HCID 70009598HCID 70009598, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of allylsulfone from Step 3 (1.78 g, 3.87 mmol) in DCM (40 mL) was added methanesulfonyl chloride (480 uL, 6.20 mmol) followed by triethylamine (730 uL, 5.2 mmol) and the reaction was stirred overnight at RT. Workup with diluted HCl and DCM afforded 2.46 g of mesylate intermediate. This mesylate intermediate (2.46 g) in THF (40 mL) was treated slowly with tBuOK 1N in THF (10 mL, 10 mmol) and the reaction was stirred 35 min at RT then diluted with water, extracted with AcOEt and DCM, dried and concentrated. The residue was purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 95:5 to 60:40) to give 1.50 g (88%) of allyl pyrane.

Workup

  1. extractionextracted with AcOEt and DCM
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by flash-chromatography over silica gel (eluted with Hexanes/AcOEt 95:5 to 60:40)

Sources & evidence

ORD record
ord-80c9fe28108c43b79429e2faaaac2a7a
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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