Methanol → Tert-butyl 7-hydroxychromane-3-carboxylate

HRID 268695Notes

Reaction equation

HRID 268695 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][O:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CO>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][O:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 59832107tert-butyl 7-(benzyloxy)-2H-chromene-3-carboxylate

Product 1

HCID 59832111Tert-butyl 7-hydroxychromane-3-carboxylateYield 62.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-butyl 7-(benzyloxy)-2H-chromene-3-carboxylate (13 g) was dissolved in ethyl acetate (15 ml) and methanol (5 ml) in a hydrogenation bottle. Pd—C (10%) (1 g) was added and the reaction mixture was hydrogenated (H2, 70 psi & RT) for overnight. After the completion of the reaction, catalyst was filtered and washed with 100 ml of ethyl acetate. Solvent was evaporated and the crude product was purified using column chromatography and ethyl acetate hexane mixture to give 6 g of pure product (48.3% overall for 2 steps).

Workup

  1. custom(H2, 70 psi & RT)
  2. customfor overnight
  3. customAfter the completion of the reaction, catalyst
  4. filtrationwas filtered
  5. washwashed with 100 ml of ethyl acetate
  6. customSolvent was evaporated
  7. customthe crude product was purified

Sources & evidence

ORD record
ord-8009cfed7c53423b9bac49313e0f3271
Source dataset
uspto-grants-2008_11
Patent number
US07446127B2

Reaction notes

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