HCID 19844335, compound → HCID 19844340, compound

HRID 867980Notes

Reaction equation

HRID 867980 reaction equation
O[C:2]([C:14]1[CH:15]=[C:16]([CH3:46])[C:17]([O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39]C2CCCCO2)=[C:18]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26]C2CCCCO2)[CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[H][H]>C(O)C.[Pd]>[C:8]1([CH:2]([C:14]2[CH:15]=[C:16]([CH3:46])[C:17]([O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][OH:39])=[C:18]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])[CH:19]=2)[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 19844335HCID 19844335, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19844340HCID 19844340, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(1-Hydroxy-1-phenyl-3,3-dimethyl-1-butyl)-3-methyl-1,2-di(2-[2-(2-tetrahydropyranyloxy)ethoxy]ethoxy)benzene (3.0 g, 0.005 mole) was dissolved in absolute ethanol (100 ml) with 10% Pd/C catalyst (0.4 g). This mixture was shaken in a Parr hydrogenator at 50 psi hydrogen pressure for 18 hours. The solution was filtered and 1N HCl (10 ml) was added to the filtrate. After 2 hours, the alcohol was evaporated in vacuo, the residual oil was dissolved in methylene chloride (50 ml) and washed with water (25 ml), brine (25 ml) and dried over MgSO4. Evaporation gave the title compound as a colorless oil (2.17 g, 95% yield).

Workup

  1. filtrationThe solution was filtered
  2. addition1N HCl (10 ml) was added to the filtrate
  3. customthe alcohol was evaporated in vacuo
  4. dissolutionthe residual oil was dissolved in methylene chloride (50 ml)
  5. washwashed with water (25 ml), brine (25 ml)
  6. dry with materialdried over MgSO4
  7. customEvaporation

Sources & evidence

ORD record
ord-c1066dc74554443aa258c8e1c97dda58
Source dataset
uspto-grants-1988_10
Patent number
US04777270

Reaction notes

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