Dimethylformamide → HCID 58484327, compound

HRID 42683Notes

Reaction equation

HRID 42683 reaction equation
C([Li])CCC.[C:6]1([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.CN(C)[CH:23]=[O:24]>CCCCCC.CCOCC>[N:16]1([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:15]=2[C:14]([CH:23]=[O:24])=[CH:13][CH:12]=[CH:11]3)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 107979951-(1-NAPHTHYL)PYRROLIDINEHCID 178418339Butyllithium

Product 1

HCID 58484327HCID 58484327, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

n-Butyllithium (14.7 ml of a 1.7 M solution in hexane) was added dropwise to a stirred solution of 1-(1-naphthyl)pyrrolidine (25.00 mmol, 5.00 g) in dry ether (50 ml) at −20° C. under argon. After 48 hours a solution of dry N,N-dimethylformamide (6.2 ml, 75.00 mmol) in ether (10 ml) was added dropwise at −78° C. to the reaction mixture. The mixture was allowed to warm to −20° C. over 4 hours, then quenched with a solution of methanol (15 ml) and allowed to warm to room temperature. The reaction mixture was diluted with ether (100 ml), washed with water (3×150 ml) and with brine (150 ml), dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography using dichloromethane as eluent to afford the aldehyde which was crystallized from hexane.

Workup

  1. customquenched with a solution of methanol (15 ml)
  2. temperatureto warm to room temperature
  3. additionThe reaction mixture was diluted with ether (100 ml)
  4. washwashed with water (3×150 ml) and with brine (150 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5daa089626d241009baf04a2be35755c
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Reaction notes

Loading…