Tetrabutylammonium Fluoride → 4-Ethynyl-3-(1-hydroxyethyl)azetidin-2-one

HRID 1090331Notes

Reaction equation

HRID 1090331 reaction equation
[OH:1][CH:2]([CH:4]1[CH:7]([C:8]#[C:9][Si](C)(C)C)[NH:6][C:5]1=[O:14])[CH3:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:8]([CH:7]1[NH:6][C:5](=[O:14])[CH:4]1[CH:2]([OH:1])[CH3:3])#[CH:9]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 132196443-(1-Hydroxyethyl)-4-(2-trimethylsilylethynyl)-2-azetidinone

Product 1

HCID 132196774-Ethynyl-3-(1-hydroxyethyl)azetidin-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 578 mg (2.74 mmol) of 3-(1-hydroxyethyl)-4-(2-trimethylsilylethynyl)-2-azetidinone, which was prepared according to T. Chiba and T. Nakai [Chem. Lett., 651 (1985)], in 5 ml of THF, 4 ml (4 mmol) of a 1M solution of tetrabutylammonium fluoride in THF was added. After stirring at room temperature for 2 hours, 10 g of silica-gel was added, the solvent was distilled away and the resultant was eluted with diethyl ether. The eluent was concentrated and purified with 10 g of silica-gel column (diethyl ether) to give 347 mg of 4-ethynyl-3-(1-hydroxyethyl)-2-azetidinone (yield: 92%).

Workup

  1. addition10 g of silica-gel was added
  2. distillationthe solvent was distilled away
  3. washthe resultant was eluted with diethyl ether
  4. concentrationThe eluent was concentrated
  5. custompurified with 10 g of silica-gel column (diethyl ether)

Sources & evidence

ORD record
ord-4242eedd9cde47719929992978cf04e6
Source dataset
uspto-grants-1992_01
Patent number
US05081238

Reaction notes

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