Diethyl Ether → HCID 11056735, compound

HRID 2294518Notes

Reaction equation

HRID 2294518 reaction equation
[OH-].[Na+].[O:3]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C@@H:4]1[O:10][C@@H:9]([C@@H:11]([C:13]([O:15]CCCCCCCCCC)=[O:14])[OH:12])[C@H:7]([OH:8])[C@H:5]1[OH:6].C(OCC)C>C1COCC1>[O:3]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C@@H:4]1[O:10][C@@H:9]([C@@H:11]([C:13]([OH:15])=[O:14])[OH:12])[C@H:7]([OH:8])[C@H:5]1[OH:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 86751624HCID 86751624, compound

Product 1

HCID 11056735HCID 11056735, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20 ml of 2.5N sodium hydroxide are added to 240 mg (0.51 mmol) of n-decyl n-decyl β-D-galactofuranoside uronate solubilized in 5 ml of THF and the mixture is allowed to stand at room temperature for 3 hours. 30 ml of ethyl ether are added and then after decanting, the aqueous phase is washed with 30 ml of ethyl ether. The aqueous phase is acidified with 50% HCl at 0° C. to pH=2 and then extracted three times with 30 ml of ethyl acetate. The organic phases are pooled, washed with 30 ml of water, dried over magnesium sulphate (2 g) and evaporated. 140 mg of n-decyl β-D-galactofuranoside uronic acid are then obtained (82% yield) in the form of a gum. *Rf=0.67 (dichloromethane/methanol-1/1-v/v) *13C NMR in CD3OD

Workup

  1. customafter decanting
  2. washthe aqueous phase is washed with 30 ml of ethyl ether
  3. customis acidified with 50% HCl at 0° C. to pH=2
  4. extractionextracted three times with 30 ml of ethyl acetate
  5. washwashed with 30 ml of water
  6. dry with materialdried over magnesium sulphate (2 g)
  7. customevaporated

Sources & evidence

ORD record
ord-83dda2718db14f3bbadb20813a876140
Source dataset
uspto-grants-1997_11
Patent number
US05688929

Reaction notes

Loading…