Acetaldehyde → HCID 15117332, compound

HRID 1029678Notes

Reaction equation

HRID 1029678 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH2:9]([N:16]1[CH2:20][CH:19]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:18][C:17]1=[O:30])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:31](=[O:33])[CH3:32].[Cl-].[Na+]>O1CCCC1>[CH2:9]([N:16]1[CH2:20][CH:19]([CH2:21][O:22][Si:23]([C:26]([CH3:27])([CH3:29])[CH3:28])([CH3:25])[CH3:24])[CH:18]([CH:31]([OH:33])[CH3:32])[C:17]1=[O:30])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 5234Sodium ChlorideHCID 2724682Lithium diisopropylamideHCID 15117331HCID 15117331, compound

Product 1

HCID 15117332HCID 15117332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of lithium diisopropylamide (4.7×10-3 mole) in tetrahydrofuran was added a solution of 1-benzyl-4-(t-butyldimethylsilyloxymethyl)-2-oxopyrrolidine (1.0 g) in tetrahydrofuran (20 ml) at -78° C. under nitrogen. The mixture was stirred for 30 minutes at -78° C., and acetaldehyde (5 ml) was added to the reaction mixture. After stirring for 30 minutes at -78° C., the solution was poured into ice water, and sodium chloride was added to saturate the aqueous phase. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The combined organic phase was dried over magnesium sulfate, and concentrated. The residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (3:1~2:1, V/V) to give 1-benzyl-3-(1-hydroxyethyl)-4-(t-butyldimethylsilyloxymethyl)-2-oxopyrrolidine (1.01 g).

Workup

  1. stirringAfter stirring for 30 minutes at -78° C.
  2. additionwas added
  3. concentrationto saturate the aqueous phase
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined organic phase was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (3:1~2:1, V/V)

Sources & evidence

ORD record
ord-fa12bdcb18c4485e9cb7f51c3016d4b2
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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