2-(4-Decyloxyphenyloxycarbonyl)-1,2,3,4-tetrahydro-6-benzyloxynaphthalene → HCID 19069952, compound

HRID 1423Notes

Reaction equation

HRID 1423 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]([CH:21]2[CH2:30][CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([O:31]CC4C=CC=CC=4)[CH:27]=3)[CH2:22]2)=[O:20])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H][H]>[Pd].O1CCCC1>[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]([CH:21]2[CH2:30][CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([OH:31])[CH:27]=3)[CH2:22]2)=[O:20])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 190700212-(4-Decyloxyphenyloxycarbonyl)-1,2,3,4-tetrahydro-6-benzyloxynaphthaleneHCID 178418361HCID 178418361, compound

Product 1

HCID 19069952HCID 19069952, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Then, 0.04 g of 5% palladium/carbon and 10 ml of a tetrahydrofuran solution containing 0.36 g of 2-(4-decyloxyphenyloxycarbonyl)-1,2,3,4-tetrahydro-6-benzyloxynaphthalene were stirred overnight at room temperature in a stream of hydrogen to decompose a benzyl protective group by hydrogenation. 5% palladium/carbon was removed using Celite as a filter aid, and the filtrate was concentrated. The concentrate obtained was purified by column chromatography to obtain 0.29 g of 2-(4-decyloxyphenyloxycarbonyl)-1,2,3,4-tetrahydro-6-hydroxynaphthalene as a white crystal (isolated yield: 97%).

Workup

  1. custom5% palladium/carbon was removed
  2. concentrationthe filtrate was concentrated
  3. customThe concentrate obtained
  4. customwas purified by column chromatography
  5. customto obtain

Sources & evidence

ORD record
ord-436174135cd54d56bccd8e2f39d9c63d
Source dataset
uspto-grants-1998_03
Patent number
US05725798

Reaction notes

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