HCID 22914134, compound → HCID 22914151, compound

HRID 1377438Notes

Reaction equation

HRID 1377438 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:6][CH:5]([C:7]2[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH3:14])[CH2:4][O:3]1>C(O)C.[Pd]>[CH3:1][C:2]1([CH3:15])[CH2:6][CH:5]([CH:7]2[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[CH:8]2[CH3:14])[CH2:4][O:3]1

Participants

4

Reactant 1

HCID 22914134HCID 22914134, compound

Product 1

HCID 22914151HCID 22914151, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

31.7 g of [rac]-2,2-dimethyl-4-(2,3,3-trimethylcyclopent-1-en-1-yl)tetrahydrofuran (from Example 4), at a purity of 92.7% (0.14 mole) were hydrogenated on a Parr shaker using 2.0 g of 5% Pd on carbon in 50 ml of ethanol. The product, 31.6 g, was distilled to afford 30 g (100% yield). BP 52°-54° C./0.2 mmHg; 1H-NMR (300 MHz), δ 0.74 (3H, s), 0.85 (3H, d, J=6.9 Hz), 0.94 (3H, s), 1.2 (1H, m), 1.19 (3H, s), 1.28 (3H, s), 1.3-1.6 (5H, m), 1.65-1.95 (2H, m), 2.33 (1H, m), 3.47 (1H, m), 3.94 (1H, m); 13C-NMR (75 MHz), δ 13.83, 22.07, 26.75, 28.29, 28.56, 28.82, 40.64, 43.57, 44.72, 45.76, 49.56, 49.69, 71.84, 81.25; IR (Neat), 2980, 1460, 1055 cm-1 ; MS (m/e), 195 (M+ -15), 137, 43 (Base);

Workup

  1. distillationThe product, 31.6 g, was distilled
  2. customto afford 30 g (100% yield)

Sources & evidence

ORD record
ord-26b60c6a7a0c4288ae699fb354e4b791
Source dataset
uspto-grants-1997_09
Patent number
US05665696

Reaction notes

Loading…