9-Hydroxy-3-(2-(3-furyl)vinyl)-spiro[5.5]undecane → HCID 15234850, compound

HRID 1757226Notes

Reaction equation

HRID 1757226 reaction equation
[OH:1][CH:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][CH:8]([CH:11]=[CH:12][C:13]3[CH:17]=[CH:16][O:15][CH:14]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3]1>C(O)C.[Pd]>[OH:1][CH:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][CH:8]([CH2:11][CH2:12][C:13]3[CH:17]=[CH:16][O:15][CH:14]=3)[CH2:9][CH2:10]2)[CH2:18][CH2:19]1

Participants

4

Reactant 1

HCID 539339589-Hydroxy-3-(2-(3-furyl)vinyl)-spiro[5.5]undecane

Product 1

HCID 15234850HCID 15234850, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2.65 g of (EZ) 9-hydroxy-3-(2-(3-furyl)vinyl)-spiro[5.5]undecane (I-ag, Ex. 31) in 50 ml of ethanol and 0.26 g of palladium on carbon (5%) was hydrogenated at room temperature and atmospheric pressure for 2 hrs, then was filtered and the filtrate evaporated to dryness to give 2.59 g of pure 9-hydroxy-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane (I-ap, Ex. 38) as white solid, mp 66°-69° C. TLC: Rf=0.42 (SiO2 plates, n-hexane/diethylether 60/40). 1H-NMR (300 MHz, CDCl3, ppm from TMS):7.35 (1H, m), 7.20 (1H, m), 6.25 (1H, m), 3.63 (1H, hept), 2.49 (2H, t), 1.95-0.95 (19H, m).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationwas filtered
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-ad18e31955f74cfaad76955052a9c7e7
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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