3,4-dihydro-2H-pyran → 2H-Pyran, tetrahydro-2-[(1-methyl-3-butynyl)oxy]-

HRID 872884

Reaction equation

HRID 872884 reaction equation
[CH3:1][CH:2]([OH:6])[CH2:3][C:4]#[CH:5].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.N1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH3:1][CH:2]([O:6][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1)[CH2:3][C:4]#[CH:5]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 929154-Pentyn-2-olHCID 161440Pyridine 4-methylbenzene-1-sulfonate

Product 1

HCID 108990812H-Pyran, tetrahydro-2-[(1-methyl-3-butynyl)oxy]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(+/−)-4-Pentyn-2-ol (5.58 ml, 59.4 mmol) and 3,4-dihydro-2H-pyran (8.08 ml, 89 mmol) were dissolved in DCM (100 ml). 4-Toluenesulfonic acid pyridine salt (1.494 g, 5.94 mmol) was added and the resulting mixture was stirred for 4 h at RT with CaCl2-tube. The mixture was concentrated. 50 ml of diethyl ether was added, extracted with brine and dried with MgSO, filtered and evaporated. The product was used in the subsequent steps without further purifications. LC-MS: [M+1]=169.23.

Workup

  1. concentrationThe mixture was concentrated
  2. addition50 ml of diethyl ether was added
  3. extractionextracted with brine
  4. dry with materialdried with MgSO
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4d067790cf264ad5b83d868f70cd05ac
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Linked notes

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