Diazomethane → 1,5-Anhydro-2,3-dideoxy-2-(methoxycarbonyl)-erythropentitol

HRID 656251Notes

Reaction equation

HRID 656251 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][C@H:5]1[CH2:10][O:9][CH2:8][C@@H:7]([C:11]([OH:13])=[O:12])[CH2:6]1>C(OCC)C.CO>[OH:4][C@H:5]1[CH2:10][O:9][CH2:8][C@@H:7]([C:11]([O:13][CH3:3])=[O:12])[CH2:6]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 68653086HCID 68653086, compound

Product 1

HCID 691244671,5-Anhydro-2,3-dideoxy-2-(methoxycarbonyl)-erythropentitol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diazomethane in diethyl ether (approx. 0.4 M) is added in excess to a solution of 23 mmol of (cis)-5-hydroxytetrahydropyran-3-carboxylic acid in 300 ml of methanol at 0° C. The mixture is stirred at 0° C. for 2 hours and then quenched with magnesium sulphate, filtered and evaporated. The crude title compound is identified by means of the Rf.

Workup

  1. customquenched with magnesium sulphate
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-1e55ef36458c48b4ac63172872a7f8d4
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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