7,9,10-Trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene → HCID 58771208, compound

HRID 63810Notes

Reaction equation

HRID 63810 reaction equation
[CH3:1][C:2]1([CH2:24][CH2:25][CH2:26][CH:27]([CH3:39])[CH2:28][CH2:29][CH2:30][CH:31]([CH3:38])[CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[O:15][C:14]2[C:5](=[C:6]3[C:11](=[C:12]([CH3:17])[C:13]=2[CH3:16])[O:10]C(CCC)O[CH:7]3[CH2:21][CH2:22][CH3:23])[CH2:4][CH2:3]1>CC(O)=O.OS(O)(=O)=O.C(Cl)Cl.[Pd]>[CH2:7]([C:6]1[C:11]([OH:10])=[C:12]([CH3:17])[C:13]([CH3:16])=[C:14]2[C:5]=1[CH2:4][CH2:3][C@@:2]([CH3:1])([CH2:24][CH2:25][CH2:26][C@H:27]([CH3:39])[CH2:28][CH2:29][CH2:30][C@H:31]([CH3:38])[CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[O:15]2)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 1

HCID 684971007,9,10-Trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene

Product 1

HCID 58771208HCID 58771208, compoundYield 105.3%

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7,9,10-trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene (Ex-1C-2) (180 mg of crude material form above) in AcOH (10 mL) and conc. H2SO4 (10 drops) was hydrogenated (H2, 50 psi, RT) with 5% Pd/C (20 mg of 50% w/w wet) at RT for 16 h. The reaction mixture was then filtered through celite. The celite was rinsed with DCM (2×2 mL). The DCM layer was concentrated by rotary evaporation to yield a light brown oil. The oil was dissolved in DCM (15 mL) and passed through a silica plug. The DCM was concentrated by rotary evaporation to yield (R,R,R)-5-butyl-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-ol (Ex-1C-3) as a cloudy yellow oil (165 mg, >100%), which was used directly without further purification.

Workup

  1. custom(H2, 50 psi, RT)
  2. customat RT
  3. customfor 16 h
  4. filtrationThe reaction mixture was then filtered through celite
  5. washThe celite was rinsed with DCM (2×2 mL)
  6. concentrationThe DCM layer was concentrated by rotary evaporation
  7. customto yield a light brown oil
  8. concentrationThe DCM was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-c0ef363922ba4be6bd1e4b73cee54562
Source dataset
uspto-grants-2016_09
Patent number
US09447006B2

Reaction notes

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