Methanol → HCID 86743200, compound

HRID 231235Notes

Reaction equation

HRID 231235 reaction equation
[F-].[Cs+].[OH:3][C:4]([CH:7]1[CH:10]([C:11]#[C:12][Si](C)(C)C)[NH:9][C:8]1=[O:17])([CH3:6])[CH3:5].O1CCCC1.CO>O.C(OCC)(=O)C>[OH:3][C:4]([C@H:7]1[C@H:10]([C:11]#[CH:12])[NH:9][C:8]1=[O:17])([CH3:5])[CH3:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25953Cesium fluorideHCID 20034791HCID 20034791, compound

Product 1

HCID 86743200HCID 86743200, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of cesium fluoride (0.05 g) in water (3 ml) is added to a mixture of 3-(1-hydroxy-1-methylethyl)-4-trimethylsilylethynyl-2-azetidinone (0.143 g) (cis-trans mixture), tetrahydrofuran (10 ml) and methanol (3 ml). The mixture is refluxed for 0.5 hour and then poured into a mixture of ethyl acetate (100 ml and water (50 ml). The organic layer is separated, washed with aqueous sodium chloride and dried over magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure. The residue is subjected to silica gel column chromatography (eluent: 30-40% ethyl acetate/60-70% hexane). The first fraction gives 0.04 g of trans-3-(1-hydroxy-1-methylethyl)-4-ethynyl-2-azetidinone.

Workup

  1. temperatureThe mixture is refluxed for 0.5 hour
  2. customThe organic layer is separated
  3. washwashed with aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customfollowed by removal of the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-dd1b56d09c4d432dad1738df41f911d2
Source dataset
uspto-grants-1989_07
Patent number
US04845210

Reaction notes

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