Triethylamine → 1-(4-Methoxybenzyl)-5-oxopyrrolidine-3-carbaldehyde

HRID 1295796Notes

Reaction equation

HRID 1295796 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5](=[O:17])[CH2:4]1.CCN(CC)CC>C(Cl)Cl>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:6]2[C:5](=[O:17])[CH2:4][CH:3]([CH:2]=[O:1])[CH2:7]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 134225594-(Hydroxymethyl)-1-[(4-methoxyphenyl)methyl]pyrrolidin-2-one

Product 1

HCID 589112571-(4-Methoxybenzyl)-5-oxopyrrolidine-3-carbaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
1 °C

Procedure

In a three necked flask, under argon, a solution 4-hydroxymethyl-1-(4-methoxy-benzyl)-pyrrolidin-2-one a2 (4.3 g, 0.018 mol) and Et3N (8.9 ml) in CH2Cl2 (25 ml) cooled down to −10° C. Pyridine-SO3 (10.1 g, 0.064 mol, 3.5 eq) is added by portions and the temperature raised up to 1° C. After 3 h at −10° C., the reaction is quenched with water (100 ml) and extracted with CH2Cl2 (3 times). The organic phase is washed with successively a 1M solution of KHSO4, water, brine, dried over MgSO4, filtered and evaporated in vacuo to give the crude aldehyde a3 (3.2 g, 87%). It is dried several times by azeotropic distillation with toluene and used as such in the next step.

Workup

  1. customthe reaction is quenched with water (100 ml)
  2. extractionextracted with CH2Cl2 (3 times)
  3. washThe organic phase is washed with successively a 1M solution of KHSO4, water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5889b8f45a1240cb8afdd895cccde051
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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