Methanol → HCID 13523632, compound

HRID 404997Notes

Reaction equation

HRID 404997 reaction equation
[CH2:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C@H:2]1[O:4][CH2:3]1.[OH-:13].[K+].[CH3:15]O>>[CH2:6]([O:5][CH2:1][C@@H:2]([OH:4])[CH2:3][O:13][CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 146296Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI)

Product 1

HCID 13523632HCID 13523632, compoundYield 98%

Conditions

Temperature
30 °C

Procedure

To a stirred solution of (S)-benzyl glycidyl ether (S)-2 (4 g, 24.3 mmol) in methanol (40 mL) was added slowly a powdered KOH (4 g; 70 mmol) at 10° C. and the reaction mixture was stirred at 30° C. temperature for 8 h, after which the solvent was evaporated under reduced pressure. The residue was dissolved in ethylacetate (50 mL), washed with water, dried over Na2SO4, and evaporated under reduced pressure. The crude product was purified by column chromatography (silica gel, petroleum ether/acetone, 90:10) to afford (S)-1-(benzyloxy)-3-methoxypropan-2-ol (S)-3 as a colorless oil (4.6 g, 98%).

Workup

  1. customafter which the solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethylacetate (50 mL)
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, petroleum ether/acetone, 90:10)

Sources & evidence

ORD record
ord-a69777300fac424d92d4b661eeeee5c1
Source dataset
uspto-grants-2014_06
Patent number
US08748660B2

Reaction notes

Loading…