HCID 66750590, compound → 941305-80-2

HRID 643914Notes

Reaction equation

HRID 643914 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][CH:14]([C:19]([CH3:21])=[CH2:20])[CH2:13][CH2:12]2)C1C=CC=CC=1.C(OC1C=C2C(=CC=1)CC(=C(C)C)CC2)C1C=CC=CC=1>CCO.[Pd]>[CH:19]([CH:14]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][C:16]=2[CH2:15]1)([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 66750590HCID 66750590, compoundHCID 66750763HCID 66750763, compound

Product 1

HCID 20828354941305-80-2

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To the mixture of 6-benzyloxy-2-isopropenyl-1,2,3,4-tetrahydronaphthalene and 6-benzyloxy-2-isopropylidene-1,2,3,4-tetrahydronaphthalene (2.37 g, crude) in EtOH (30 mL) is added 10% Pd/C (550 mg) and it is hydrogenated at RT and at 1 atm for 24 h. The mixture is filtered through Celite, and the filtrate is concentrated and purified to give the title compound: 1H NMR (CDCl3) δ 0.95 (d, J=6 Hz, 6H), 1.31-1.41 (m, 1H), 1.42-1.46 (m, 1H), 1.56-1.62 (m, 1H), 1.87-1.92 (m, 1H), 2.39-2.45 (m, 1H), 2.69-2.77 (m, 3H), 4.43 (s, 2H), 6.55 (d, J=2.5 Hz, 1H), 6.58 (d, J=2.5, 8 Hz, 1H), 6.93 (d, J=8 Hz, 1H), 7.31-7.43 (m, 5H); (M−H)−=189.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationthe filtrate is concentrated
  3. custompurified

Sources & evidence

ORD record
ord-f3db59627cee4141977fbdb1f2e3eeb3
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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