4-(Dimethylamino)Benzaldehyde → HCID 23050470, compound

HRID 1651814Notes

Reaction equation

HRID 1651814 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].C([Li])CCC.[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]([OH:19])[C:3]#[C:2][C:1]([O:5][CH3:6])=[O:4])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 74794-(Dimethylamino)BenzaldehydeHCID 13536Methyl propiolateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 23050470HCID 23050470, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.7 ml (80 mmol) of methyl propiolate in 80 ml of tetrahydrofuran was treated at -78° under argon with 53.1 ml of n-butyllithium (1.6M in hexane). The mixture was stirred at -78° for 10 minutes and then a solution of 11.94 g (80 mmol) of 4-dimethylaminobenzaldehyde in 80 ml of tetrahydrofuran was added within 30 minutes. The reaction mixture was stirred at -78° for a further 20 minutes then brought to room temperature and treated with 120 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ether, the combined organic phases were washed in sequence with saturated sodium chloride solution and with water, dried over sodium sulphate and concentrated. The residue was purified by flash chromatography on 1000 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1). There was obtained methyl 4-[4-(dimethylamino)phenyl)-4-hydroxy-2-butynoate as a red oil.

Workup

  1. stirringThe reaction mixture was stirred at -78° for a further 20 minutes
  2. customthen brought to room temperature
  3. extractionThe aqueous phase was extracted twice with ether
  4. washthe combined organic phases were washed in sequence with saturated sodium chloride solution and with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on 1000 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-ce8311e45d274a26a407b0fb3ea0509d
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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