Triethylamine → HCID 13583686, compound

HRID 2253698Notes

Reaction equation

HRID 2253698 reaction equation
[C:1]1([CH:7]2[NH:10][C:9](=[O:11])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>CN(C=O)C>[C:1]1([CH:7]2[N:10]([Si:16]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:18])[CH3:17])[C:9](=[O:11])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 5688184-Phenylazetidin-2-one

Product 1

HCID 13583686HCID 13583686, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Phenylazetidin-2-one (10.4 gm, 71.0 mmole) (Graf, Chem. Ber, 111 (1963); Durst et al. J. Org. Chem., 35, 2043 (1970)) was dissolved in DMF (200 ml) and was treated with tert.-butyldimethylsilyl chloride (12.8 gm, 85 mmol) and triethylamine (11.8 ml, 85 mmol). The mixture was stirred at room temperature for 16 hrs. and taken up in either (500 ml). The ethereal solution was washed with 1N hydrochloric acid (1×100 ml), water (2×50 ml) and brine (1×50 ml). After the solution was dried (anhyd. magnesium sulfate) and evaporated, the residue was flash chromatographed on SiO2 -gel column. Elution with 15% ethyl acetate in hexane afforded 4-phenyl-1-(tert.-butyldimethylsilyl)azetidin-2-one (18.4 gm, 99%) as an oil which solidified on standing.

Workup

  1. washThe ethereal solution was washed with 1N hydrochloric acid (1×100 ml), water (2×50 ml) and brine (1×50 ml)
  2. dry with materialAfter the solution was dried (anhyd. magnesium sulfate)
  3. customevaporated
  4. customchromatographed on SiO2 -gel column
  5. washElution with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4b294b7634d34dd7bbc0f28f7ff92d0f
Source dataset
uspto-grants-1993_08
Patent number
US05232929

Reaction notes

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