HCID 54686174, compound → HCID 67809616, compound

HRID 1757045Notes

Reaction equation

HRID 1757045 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[O:15][C:14](=[O:16])[CH:13]=[C:12]([OH:17])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C>[Si:1]([O:8][CH2:9][CH:10]1[O:15][C:14](=[O:16])[CH:13]=[C:12]([OH:17])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 54686174HCID 54686174, compound

Product 1

HCID 67809616HCID 67809616, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-t-Butyldimethylsilyloxymethyl-4-hydroxypyran-2-one (25.9 parts) was dissolved in ethanol (1600 parts) and the solution purged with nitrogen. 10% Palladium on carbon catalyst (5.2 parts) was added and the mixture hydrogenated at 20°-25° C. When the reaction was complete as judged by GC analysis the catalyst was filtered off and the solvent was distilled off under reduced pressure at 40° C. to leave 6-t-butyldimethylsilyloxymethyl-5,6-dihydro-4-hydroxy pyran-2-one (23.0 parts, 90%) m.p. 119°-122° C. as a light brown residue.

Workup

  1. customthe solution purged with nitrogen
  2. addition10% Palladium on carbon catalyst (5.2 parts) was added
  3. customhydrogenated at 20°-25° C
  4. filtrationwas filtered off
  5. distillationthe solvent was distilled off under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-7e57db42dd684ec197c243e0dd8dcf0e
Source dataset
uspto-grants-1995_08
Patent number
US05443970

Reaction notes

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