Piperonal → HCID 23050448, compound

HRID 1651836Notes

Reaction equation

HRID 1651836 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.[CH2:18]1[O:28][C:27]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][C:20]=2[O:19]1.[Cl-].[NH4+]>O1CCCC1>[OH:24][CH:23]([C:22]1[CH:25]=[CH:26][C:27]2[O:28][CH2:18][O:19][C:20]=2[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 8438PiperonalHCID 25517Ammonium ChlorideHCID 23050500HCID 23050500, compoundHCID 178418339Butyllithium

Product 1

HCID 23050448HCID 23050448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.9 g (40 mmol) of 2-(2-methoxyethoxy)-ethyl propiolate in 60 ml of tetrahydrofuran was treated at -78° under argon with 25 ml of n-butyllithium (1.6M in hexane). The mixture was stirred at -78° for 10 minutes and then a solution of 6 g (40 mmol) of 3,4-methylenedioxy-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 100 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 600 g of silica gel (elution agent methylene chloride/ether 4:1). There was obtained 2-(2-methoxyethoxy)ethyl 4-hydroxy-4-[3,4(methylenedioxy)phenyl]-2 -butynoate as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred at -78° for a further 30 minutes
  2. customthen brought to room temperature
  3. extractionwas 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 600 g of silica gel (elution agent methylene chloride/ether 4:1)

Sources & evidence

ORD record
ord-9b973a23a90347b6994cddb014f2376c
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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