3,4,5-Trimethoxybenzaldehyde → HCID 23050479, compound

HRID 1651834Notes

Reaction equation

HRID 1651834 reaction equation
[C:1]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])(=[O:4])[C:2]#[CH:3].C([Li])CCC.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH:23]=[O:24].[Cl-].[NH4+]>O1CCCC1>[OH:24][CH:23]([C:22]1[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:20]([O:19][CH3:18])[CH:21]=1)[C:3]#[C:2][C:1]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])=[O:4]

Participants

6

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 25517Ammonium ChlorideHCID 23050500HCID 23050500, compoundHCID 178418339Butyllithium

Product 1

HCID 23050479HCID 23050479, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10 g (58 mmol) of 2-(2-methoxyethoxy)ethyl propiolate in 80 ml of tetrahydrofuran was treated at -78° under argon with 36 ml of n-butyllithium (1.6M in hexane). The mixture was stirred at -78° for 10 minutes and then a solution of 11.4 g (58 mmol) of 3,4,5-trimethoxy-benzaldehyde in 60 ml of tetrahydrofuran was added within 30 minutes. The reaction mixture was stirred at -78° for a further 30 minutes, then brought to room temperature and treated with 150 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ether. The combined organic phases were washed in succession 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/ether 4:1). There was obtained 2-(2-methoxyethoxy)ethyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate as a red oil.

Workup

  1. stirringThe reaction mixture was stirred at -78° for a further 30 minutes
  2. custombrought to room temperature
  3. extractionThe aqueous phase was extracted twice with ether
  4. washThe combined organic phases were washed in succession 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/ether 4:1)

Sources & evidence

ORD record
ord-004523e4b1fe4094ba90585e8fe9759d
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

Loading…