Potassium Carbonate → tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

HRID 234173Notes

Reaction equation

HRID 234173 reaction equation
C([O:4][CH2:5][C@H:6]1[O:11][C:10]([CH3:13])([CH3:12])[O:9][C@@H:8]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:7]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][CH2:5][C@H:6]1[O:11][C:10]([CH3:12])([CH3:13])[O:9][C@@H:8]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:7]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 9839384(4R-cis)-6-[(Acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester

Product 1

HCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester obtained in step (a) above (22.65 g, 75 mmole) in methanol (250 ml) was added powdered anhydrous potassium carbonate (5.17 g, 37.5 mmole) in one portion. The resulting heterogeneous solution was stirred vigorously for 30 minutes to complete the hydrolysis. The progress of the reaction was followed by TLC and GC analysis. (TLC: Rf=0.54 for acetyloxy starting material; Rf=0.26 for the title compound (silica gel, Ethyl acetate:Hexane, 1:1, visualized by Ce(SO4)2 spray).

Workup

  1. customthe hydrolysis

Sources & evidence

ORD record
ord-aff9fc869d4f438f9f813b346212efc7
Source dataset
uspto-grants-1997_01
Patent number
US05594153

Reaction notes

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