Sodium Chloride → 2H-Pyran, tetrahydro-2-(10-undecyn-1-yloxy)-

HRID 1684502Notes

Reaction equation

HRID 1684502 reaction equation
[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11].[OH2:13].[C:14]1(C)C=[CH:18][C:17](S(O)(=O)=O)=[CH:16][CH:15]=1.[Cl-].[Na+]>ClCCl.O1C=CCCC1>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 7601510-Undecyn-1-olHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 1035662H-Pyran, tetrahydro-2-(10-undecyn-1-yloxy)-Yield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80803,4-dihydro-2H-pyranSolvent

Procedure

17.5 g (0,104 mol) of undec-10-yn-1-ol were dissolved in 100 ml of dichloromethane and 25 ml of dihydropyran, and a catalytic amount (spatula tipful) of p-toluenesulfonic acid monohydrate was added. The reaction mixture was left to stand overnight at room temperature and poured into saturated aqueous sodium chloride solution. Extraction with dichloromethane (3×), drying (Na2SO4) of the combined organic phases and flash chromatography on silica gel (n-heptane/ethyl acetate=10:1) gave 24 g (92% of theory) of 11-tetrahydropyranyloxyundecyne.

Workup

  1. waitThe reaction mixture was left
  2. extractionExtraction with dichloromethane (3×)
  3. dry with materialdrying (Na2SO4) of the combined organic phases and flash chromatography on silica gel (n-heptane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-195653d093434236aea09509bb0d9405
Source dataset
uspto-grants-1997_06
Patent number
US05641767

Reaction notes

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