3,4,5-Trimethoxybenzaldehyde → HCID 54523158, compound

HRID 1651826Notes

Reaction equation

HRID 1651826 reaction equation
[C:1]([O:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])(=[O:4])[C:2]#[CH:3].C([Li])CCC.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH:21]=[O:22].[Cl-].[NH4+]>O1CCCC1>[OH:22][CH:21]([C:20]1[CH:23]=[C:24]([O:28][CH3:29])[C:25]([O:26][CH3:27])=[C:18]([O:17][CH3:16])[CH:19]=1)[C:3]#[C:2][C:1]([O:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])=[O:4]

Participants

6

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 25517Ammonium ChlorideHCID 14249453HCID 14249453, compoundHCID 178418339Butyllithium

Product 1

HCID 54523158HCID 54523158, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.6 g (4g mmol) of 3-methyl-2-butenyl propiolate in 60 ml of tetrahydrofuran was treated at -78° under argon with 30 ml of n-butyllithium (1.6M in hexane). The mixture was stirred at -78° for 10 minutes and then a solution of 9.4 g (48 mmol) of 3,4,5-trimethoxybenzaldehyde in 80 ml of tetrahydrofuran was added within 30 minutes. The reaction mixture was stirred at -78° for a further 1 hour, then brought to room temperature and treated with 120 ml of saturated ammonium chloride solution The aqueous phase was extracted twice with ether. The 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 700 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1). There was obtained 3-methyl-2-butenyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred at -78° for a further 1 hour
  2. custombrought to room temperature
  3. extractionwas extracted twice with ether
  4. washThe 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 700 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-13a10cf524504695a631459fde411c48
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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