HCID 69682309, compound → HCID 10180469, compound

HRID 394925Notes

Reaction equation

HRID 394925 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:15]=[CH:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2>C(O)C.[Pd]>[CH3:1][C:2]1([CH3:31])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:15][CH2:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 1

HCID 69682309HCID 69682309, compound

Product 1

HCID 10180469HCID 10180469, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

200 mg of (RS)-4-[3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-oct-1-enyl]-benzoic acid were dissolved in 20 ml of absolute ethanol and 60 mg of 30% Pd on carbon were added. The reaction flask was purged from the oxygen by vacuum and hydrogen filling (two times). The mixture was subjected to atmospheric H2 pressure for 6 hours. The reaction mixture was filtered on a pad of Celite and concentrated in vacuo. The product was purified by preparative tic (SiO2, 5% methanol/methylene chloride), giving 140 mg of the titled compound as a white solid. 1H NMR (CDCl3): 7.99 (d, J=8.3 Hz, 2H), 7.21 (d, J=8.1 Hz, 1H), 7.19 (d, J=8.3 Hz, 2H), 7.02 (d, J=1.8 Hz, 1H), 6.89 (dd, J=8.1, 1.8 Hz, 1H), 2.60-2.35 (m, 3H), 2.05-1.80 (m, 2H), 1.68 (s, 4H), 1.60-1.45 (m, 2H), 1.28 (s, 3H), 1.27 (s, 9H), 1.30-1.10 (m, 6H), 0.82 (t, J=6.7 Hz, 3H).

Workup

  1. customThe reaction flask was purged from the oxygen by vacuum and hydrogen filling (two times)
  2. filtrationThe reaction mixture was filtered on a pad of Celite
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by preparative tic (SiO2, 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-3d588064eeeb42ddb5dace95668b68a0
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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