Acetaldehyde → HCID 12874036, compound

HRID 444544Notes

Reaction equation

HRID 444544 reaction equation
C([N-]C(C)C)(C)C.[Li+].[O:9]=[C:10]1[N:17]2[C:12]([CH3:20])([CH2:13][CH2:14][O:15][C:16]2([CH3:19])[CH3:18])[CH2:11]1.[CH:21](=[O:23])[CH3:22].[Cl-].[Na+]>O1CCCC1.O>[O:9]=[C:10]1[N:17]2[C:12]([CH3:20])([CH2:13][CH2:14][O:15][C:16]2([CH3:19])[CH3:18])[CH:11]1[CH:21]([OH:23])[CH3:22]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 5234Sodium ChlorideHCID 2724682Lithium diisopropylamideHCID 12874034HCID 12874034, compound

Product 1

HCID 12874036HCID 12874036, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 1.1 equivalents of freshly prepared lithium diisopropylamide in anhydrous tetrahydrofuran under a nitrogen atmosphere at -78° is added a solution of 8-oxo-2,2,6-trimethyl- 3-oxa-1-azabicyclo[4.2.0]octane in anhydrous tetrahydrofuran which has been cooled to -78° C. After two minutes, the resulting lithium enolate is treated with excess acetaldehyde. The solution is stirred for 30 minutes at -78° and then poured into water. The aqueous phase is saturated with sodium chloride and extracted with ethyl acetate. The combined ethyl acetate solutions are dried over magnesium sulfate and filtered. The filtrate is evaporated under reduced pressure to give the crude product. Purification by chromatography on silica gel using ethylacetate/benzene gives 8-oxo-2,2,6-trimethyl-7-(1-hydroxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined ethyl acetate solutions are dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate is evaporated under reduced pressure
  5. customto give the crude product
  6. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-a510198c04074f4ca00c9773351d2b2a
Source dataset
uspto-grants-1981_04
Patent number
US04264621

Reaction notes

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