Pyridine → 1-(t-Butyldimethylsilyl)-4-(2-oxoethyl)-2-azetidinone

HRID 867578Notes

Reaction equation

HRID 867578 reaction equation
N1C=CC=CC=1.[Si:7]([N:14]1[CH:17]([CH2:18][CH2:19][OH:20])[CH2:16][C:15]1=[O:21])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>C(Cl)Cl>[Si:7]([N:14]1[CH:17]([CH2:18][CH:19]=[O:20])[CH2:16][C:15]1=[O:21])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 1049PyridineHCID 13104623N-(t-butyldimethylsilyl)-4-(2-hydroxyethyl)-azetidin-2-one

Product 1

HCID 128047181-(t-Butyldimethylsilyl)-4-(2-oxoethyl)-2-azetidinoneYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Anhydrous CrO3 (1.94 g, 19.38 mmol) is added to a solution of anhydrous pyridine (3.07 g, 38.76 mmol) in anhydrous CH2Cl2 (50 ml). The resulting mixture is stirred at r.t. for 15 min. A solution of 1-(t-butyldimethylsilyl)-4-(2-hydroxyethyl)-2-azetidinone (0.74 g, 3.23 mmol) in anhydrous CH2Cl2 5 ml is added all at once. After stirring for 5 min, the CH2Cl2 solution is separated from a dark gummy precipitate which is washed with more CH2Cl2. The combined CH2Cl2 solution is evaporated under vacuum. The residue is taken up in ether filtered and washed with 5% NaHCO3, 5% HCl, 5%NaHCO3 and brine then dried and evaporated to give the aldehyde (0.543 g 74%).

Workup

  1. stirringAfter stirring for 5 min
  2. customthe CH2Cl2 solution is separated from a dark gummy precipitate which
  3. washis washed with more CH2Cl2
  4. customThe combined CH2Cl2 solution is evaporated under vacuum
  5. filtrationfiltered
  6. washwashed with 5% NaHCO3, 5% HCl, 5%NaHCO3 and brine
  7. customthen dried
  8. customevaporated

Sources & evidence

ORD record
ord-c3117c64dfc14b3398e333b21e7a11d6
Source dataset
uspto-grants-1988_10
Patent number
US04775669

Reaction notes

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