HCID 15715412, compound → HCID 15715413, compound

HRID 1770312Notes

Reaction equation

HRID 1770312 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:12]2[C:17](=[O:18])[O:16][C:15]([CH3:20])([CH3:19])[O:14][C:13]=2[CH:21]=1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH3:20][C:15]1([CH3:19])[O:14][C:13]2[CH:21]=[C:9]([OH:8])[CH:10]=[C:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:12]=2[C:17](=[O:18])[O:16]1

Participants

4

Reactant 1

HCID 15715412HCID 15715412, compound

Product 1

HCID 15715413HCID 15715413, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Compound (12) (500 mg, 1.32 mmol) was hydrogenated over Pd(OH)2 (20%, 95 mg, ca. 0.1 eq.) in EtOH (15 mL) at atmospheric pressure for 12 hrs. Filtration through Celite™ and concentration left 387 mg (100%) of white solids. m.p. 100°-102° C. IR (CHCl3) 3100-3400, 3020, 2930, 1715, 1615, 1590, 1450, 1390, 1295, 1170, 1050 cm-1 ; 1H NMR (CDCl3, 250 MHz) δ6.42 (d, 1H, J=2.4 HZ, ArH), 6.27 (d, 1H, J=2.4 Hz, ArH), 5.50 (br s, 1H, OH), 3.04 (br t 2H, J=7.7 Hz), 1.69 (s, 6H, CH3), 1.20-1.65 (m, 1OH), 0.88 (t, 3H, J=7.2 Hz, CH3).

Workup

  1. filtrationFiltration
  2. concentrationthrough Celite™ and concentration
  3. waitleft 387 mg (100%) of white solids

Sources & evidence

ORD record
ord-92a9e00aff3a4ef0a58eeecb05aa1e6e
Source dataset
uspto-grants-1995_01
Patent number
US05386019

Reaction notes

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