(1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one → (1RS,2RS,6-SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]dec-4-en-3-one

HRID 407838Notes

Reaction equation

HRID 407838 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:24])[CH:14]2[CH:19]([C:20]=1[O:21][CH3:22])[CH:18]1[O:23][CH:15]2[CH:16]=[CH:17]1)[CH3:2]>CO.[Pd]>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:24])[CH:14]2[CH:19]([C:20]=1[O:21][CH3:22])[CH:18]1[O:23][CH:15]2[CH2:16][CH2:17]1)[CH3:2]

Participants

4

Reactant 1

HCID 67283452(1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one

Product 1

HCID 67283587(1RS,2RS,6-SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]dec-4-en-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one (0.052 g, 0.16 mmol) in methanol (10 ml) is added 5% palladium on carbon (10 mg). The reaction is stirred under an atmosphere of hydrogen for 90 minutes. The reaction is filtered through diatomaceous earth and the filter pad is washed with ethyl acetate (10 ml). The solvent is removed under reduced pressure to yield (1RS,2RS,6-SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]dec-4-en-3-one.

Workup

  1. filtrationThe reaction is filtered through diatomaceous earth
  2. washthe filter pad is washed with ethyl acetate (10 ml)
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-c8dfa95d3a6f48d987885baa32711571
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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