8-Methoxy-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde → HCID 22318122, compound

HRID 497030Notes

Reaction equation

HRID 497030 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=[C:5]([CH:13]=[O:14])[CH:4]=1.[CH3:15][Mg]Cl>O1CCCC1>[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=[C:5]([CH:13]([OH:14])[CH3:15])[CH:4]=1

Participants

4

Reactant 2

HCID 6065788-Methoxy-2,3-dihydro-1,4-benzodioxine-6-carbaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 22318122HCID 22318122, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 250 mL round-bottomed flask, 0.60 g (3.1 mmol) of 10 was dissolved in 15 mL of anhydrous tetrahydrofuran. The solution was cooled to 0° C. and treated with 1.1 mL (3.3 mmol) of 3M methyl magnesium chloride in THF. The reaction was stirred for a few minutes then quenched with a 1N HCl solution. The mixture was extracted with ethyl acetate. The organic extract was washed with brine, dried (Na2SO4), filtered, and evaporated in vacuo to afford the alcohol 11.

Workup

  1. customthen quenched with a 1N HCl solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4bbe1fdfb2d9459c826e191e07e55b43
Source dataset
uspto-grants-2005_09
Patent number
US06949544B2

Reaction notes

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