Sodium Sulfate → Methyl 4-(hydroxymethyl)oxane-4-carboxylate

HRID 2426964Notes

Reaction equation

HRID 2426964 reaction equation
[O:1]1[CH2:6][CH2:5][C:4]([C:11](OC)=[O:12])([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:12][CH2:11][C:4]1([C:7]([O:9][CH3:10])=[O:8])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 24436Sodium SulfateHCID 11063483Dimethyl Tetrahydropyran-4,4-dicarboxylate

Product 1

HCID 67253252Methyl 4-(hydroxymethyl)oxane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an atmosphere of argon, to a solution of lithium aluminum tri(tert-butoxy)hydride (1.93 g) in tetrahydrofuran (15 mL) was added a solution of dimethyl tetrahydro-2H-pyran-4,4-dicarboxylate (606 mg) in tetrahydrofuran (5 mL) and the mixture was stirred at room temperature for an hour. To the reaction mixture was added an an aqueous saturated sodium sulfate solution till being cloudy. An insoluble matter was filtered and the filtrate was concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1→1:2→1:4→ethyl

Workup

  1. filtrationAn insoluble matter was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe obtained residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-1cb772ebd4a04056a21e5f0a08731bfb
Source dataset
uspto-grants-2011_06
Patent number
US07968572B2

Reaction notes

Loading…