Acetic Acid → HCID 9964662, compound

HRID 2415431Notes

Reaction equation

HRID 2415431 reaction equation
Br[CH2:2][C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18]C=O)=[CH:13][CH:12]=1.C(O)(=O)C>O>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH:7]2[O:6][C:4](=[O:5])[C:3](=[CH2:8])[CH2:2]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl esterHCID 111266073-(4-Methoxyphenyl)propanal

Product 1

HCID 9964662HCID 9964662, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension formed from metallic tin (730 mg, 6.15 mmoles), diethyl ether (12.5 ml) and water (3.1 ml) were added 1.10 g (6.15 mmoles) of methyl 2-bromomethyl-2-propenoate and 1.11 g (6.77 mmoles) of 3-(4-methoxyphenyl) propanal, with catalytic quantities of acetic acid. The mixture was kept warm at 50° C. with stirring for 9 hours. At the end of this time it was poured into water (200 ml) and an extraction was performed with diethyl ether (3×100 ml). The result was dried over anhydrous sodium sulphate and vacuum concentrated, giving an oil 780 mg (70% yield) of 5-[2-(4-methoxyphenyl)-ethyl]-3-metylene-dihydrofuran-2-one [(I), R═CH3; R1═H].

Workup

  1. extractionan extraction
  2. dry with materialThe result was dried over anhydrous sodium sulphate and vacuum
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b056b5f8001d457baf7324a76635d931
Source dataset
uspto-grants-2004_11
Patent number
US06818780B2

Reaction notes

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