Ethyl diethoxyacetate → HCID 66643980, compound

HRID 1474287Notes

Reaction equation

HRID 1474287 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:13]([O:15][CH:16]([O:22]CC)[C:17](OCC)=O)C>C[N+]([O-])=O.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[O:8][CH3:9])[CH:17]([C:16]([O:15][CH3:13])=[O:22])[O:12][CH2:11][CH2:10]2

Participants

5

Reactant 2

HCID 80169Ethyl diethoxyacetateHCID 230022542-(3-bromo-4-methoxyphenyl)ethanol

Product 1

HCID 66643980HCID 66643980, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6375NitromethaneSolvent

Procedure

To an ice-cooled mixture of 2-[3-bromo-4-(methyloxy)phenyl]ethanol (9.5 g, 41 mmol) and ethyl bis(ethyloxy)acetate (8.7 g, 48 mmol) in 60 mL of CH3NO2 was added TiCl4 (31.2 g, 169 mmol) over a period of 20 min. After stirring for 10 min, the ice bath was removed and the mixture was allowed to stir at room temperature over night. The mixture was poured onto ice/aqueous 1N HCl. Extracted by DCM and backwashed with 1N HCl and brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified via column chromatography to give methyl 6-bromo-7-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylate.

Workup

  1. customthe ice bath was removed
  2. stirringto stir at room temperature over night
  3. additionThe mixture was poured onto ice/aqueous 1N HCl
  4. extractionExtracted by DCM
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified via column chromatography

Sources & evidence

ORD record
ord-0df1294a36ed49319cb1f0f5fabba032
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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