Hydrochloric Acid → [(3R)-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl]acetaldehyde

HRID 2281306Notes

Reaction equation

HRID 2281306 reaction equation
Cl.[O:2]1CCO[CH:3]1[CH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[O:13][C@H:12]([CH3:19])[CH2:11]2>O1CCOCC1>[CH3:19][C@@H:12]1[CH2:11][C:10]2[C:15](=[CH:16][CH:17]=[C:8]([CH2:7][CH:3]=[O:2])[CH:9]=2)[C:14](=[O:18])[O:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86693034(3R)-6-(1,3-dioxolan-2-ylmethyl)-3-methyl-3,4-dihydro-1H-isochromen-1-one

Product 1

HCID 86693035[(3R)-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl]acetaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1:1 solution of dioxane:3 N HCl was added to a flask containing (3R)-6-(1,3-dioxolan-2-ylmethyl)-3-methyl-3,4-dihydro-1H-isochromen-1-one (780 mg, 3.2 mmol). The reaction was then stirred at room temperature overnight. The crude reaction mixture was then partitioned between water and DCM. The organic layer was washed with saturated sodium bicarbonate solution, followed by brine. The organic layer was then dried with magnesium sulfate, filtered and concentrated to afford (R)-2-(3-methyl-1-oxoisochroman-6-yl)acetaldehyde which was used directly without further purification.

Workup

  1. customThe crude reaction mixture
  2. customwas then partitioned between water and DCM
  3. washThe organic layer was washed with saturated sodium bicarbonate solution
  4. dry with materialThe organic layer was then dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-92e7032aeedc4ff58d814d53c4950150
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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