Methyl 2-acetyl-7-benzyloxy-8-n-propylchroman-2-carboxylate → Methyl 2-acetyl-7-hydroxy-8-n-propylchroman-2-carboxylate

HRID 1285264Notes

Reaction equation

HRID 1285264 reaction equation
[C:1]([C:4]1([C:25]([O:27][CH3:28])=[O:26])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]([O:14]CC3C=CC=CC=3)=[CH:9][CH:10]=2)[O:5]1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([C:4]1([C:25]([O:27][CH3:28])=[O:26])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]([OH:14])=[CH:9][CH:10]=2)[O:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 20250461Methyl 2-acetyl-7-benzyloxy-8-n-propylchroman-2-carboxylate

Product 1

HCID 20250456Methyl 2-acetyl-7-hydroxy-8-n-propylchroman-2-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

920 mg (2.41 mmole) of the compound from Example 38 was dissolved in 50 ml methanol and 92 mg 5% palladium on carbon added. The suspension was hydrogenated at room temperature and 2 psi for 2.5 hours. Removal of the catalyst by filtration and removal of methanol by rotary evaporation gave 640 mg (91%) of the title compound as a light orange oil, which began to crystallize on standing, homogeneous by thin layer chromatography in 20% ethyl acetate-hexane.

Workup

  1. customwas hydrogenated at room temperature
  2. customRemoval of the catalyst
  3. filtrationby filtration and removal of methanol
  4. customby rotary evaporation

Sources & evidence

ORD record
ord-21dffa57e2f0498593ad51ad564b073c
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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