HCID 67809616, compound → HCID 19389468, compound

HRID 1757046Notes

Reaction equation

HRID 1757046 reaction equation
[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]>C(O)C>[Si:1]([O:8][CH2:9][CH:10]1[O:15][C:14](=[O:16])[CH2:13][CH:12]([OH:17])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 67809616HCID 67809616, compound

Product 1

HCID 19389468HCID 19389468, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-t-Butyldimethylsilyloxymethyl-5,6-dihydro-4-hydroxy pyran-2-one (26.3 parts) was dissolved in ethanol (500 parts) and heated to 45° C.-55° C. Raney nickel (6.6 parts) was washed caustic free with water and then water free with ethanol and added to the pyran-2-one solution under a blanket of nitrogen. Hydrogen was passed through the rapidly stirred mixture until the reaction was complete, as judged by GC analysis. The catalyst was filtered off and the solvent removed at 40° C./20 mm to leave 6-t-butyldimethylsilyloxymethyl-4-hydroxytetrahydro pyran-2-one (25.7 parts, 96%, cis/trans ratio 82/18) as a greenish oil which solidified on standing.

Workup

  1. temperatureheated to 45° C.-55° C
  2. washRaney nickel (6.6 parts) was washed caustic free with water
  3. additionwater free with ethanol and added to the pyran-2-one solution under a blanket of nitrogen
  4. filtrationThe catalyst was filtered off
  5. customthe solvent removed at 40° C./20 mm

Sources & evidence

ORD record
ord-10fca33d8a424f7f8797511275ff703f
Source dataset
uspto-grants-1995_08
Patent number
US05443970

Reaction notes

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