Sodium Carbonate → 4-Ethoxybut-2-yn-1-ol

HRID 237862Notes

Reaction equation

HRID 237862 reaction equation
[CH2:1]([O:3][CH2:4][C:5]#[C:6][CH2:7][O:8][CH:9]1[CH2:14]CCC[O:10]1)[CH3:2].O.[C:16]1(C)[CH:21]=[CH:20][C:19](S(O)(=O)=O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:7][O:8][C:9]([CH3:14])=[O:10].[CH3:20][CH2:21][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:1]([O:3][CH2:4][C:5]#[C:6][CH2:7][OH:8])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 685294632-(4-Ethoxy-but-2-ynyloxy)-tetrahydro-pyran

Product 2

HCID 127868104-Ethoxybut-2-yn-1-olYield 385.9%HCID 23449302Methyl acetate hexaneYield 1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-ethoxy-but-2-ynyloxy)-tetrahydro-pyran (0.5 g, 2.52 mmol) in methanol (10 mL) was added p-toluenesulfonic acid monohydrate (p-TSOH) (0.086 g, 0.454 mmol). The reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture was poured into aqueous sodium carbonate and extracted with methyl acetate. The organic layers were combined, dried (Na2SO4) and concentrated. Silica gel chromatography (1-10% MeOAc/hexane) provided 0.2 g of 4-ethoxy-but-2-yn-1-ol as a clear oil.

Workup

  1. extractionextracted with methyl acetate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-04be88845d1f4d6d9b54e5d1406b7d8f
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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