Ethyl Acetate → HCID 22048326, compound

HRID 1833182Notes

Reaction equation

HRID 1833182 reaction equation
C(OC([N:6]1[CH:15]=[C:14]([CH:16]=[O:17])[C:13]2[C:8](=[CH:9][C:10]([O:26][CH3:27])=[C:11]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH:12]=2)[CH:7]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][CH3:37])[CH:30]=1)=O)C.[OH-].[K+].C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>CO>[C:23]([O:22][CH2:21][CH2:20][CH2:19][O:18][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:26][CH3:27])[CH:7]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][CH3:37])[CH:30]=1)[NH:6][CH:15]=[C:14]2[CH:16]=[O:17])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 21226206Ethyl acetate hexane2×HCID 86595640HCID 86595640, compound

Product 1

HCID 22048326HCID 22048326, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-(3-acetoxy-propoxy)-1-(3-ethoxy-benzyl)-4-formyl-7-methoxy-1H-isoquinoline-2-carboxylic acid ethyl ester (130 mg, 0.25 mmol) in methanol (3.5 mL) was added powdered potassium hydroxide (85.5 mg, 1.53 mmol) at room temperature. The mixture was stirred at room temperature for 14 hrs. The solvent was evaporated and the residue was diluted with water (20 mL). The aqueous phase was extracted with ethyl acetate (2×20 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a crude oil. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexane, 75% ethyl acetate/hexane, ethyl acetate) afforded 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-ethoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde (120 mg, 42% yield).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water (20 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×20 mL)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a crude oil

Sources & evidence

ORD record
ord-6fb7dbeb44494be39e4524d8eb9a671c
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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