1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-ol → 1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-one

HRID 1403467Notes

Reaction equation

HRID 1403467 reaction equation
[C:1]1([CH:7]([OH:18])[C:8]#[C:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl>[C:1]1([C:7](=[O:18])[C:8]#[C:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 706652771-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-ol

Product 1

HCID 109117581-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-oneYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-ol (3.0 g, 12.2 mmol) in DCM (50 mL) was added DMP (10.0 g, 24.4 mmol). The resulting solution was stirred for 30 min at room temperature and then the reaction mixture was poured into NaHCO3/NaS2O3 solution and stirred for overnight, extracted with DCM (3×150 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to give a residue. The residue was purified by silica gel column chromatography (3% ethyl acetate in petroleum ether) to afford 1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-one as a light yellow oil (2.4 g).

Workup

  1. stirringstirred for overnight
  2. extractionextracted with DCM (3×150 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThe residue was purified by silica gel column chromatography (3% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-7be7eb5c217e4966b6cd620c7721466e
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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