HCID 22894817, compound → HCID 15875321, compound

HRID 1532531Notes

Reaction equation

HRID 1532531 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:15][C:16](=[O:18])[CH3:17])[C:12]([CH3:14])=[CH2:13])=[CH:7][C:6]=1[O:19][CH3:20])(=[O:3])[CH3:2]>CCO.O=[Pt]=O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:15][C:16](=[O:18])[CH3:17])[CH:12]([CH3:14])[CH3:13])=[CH:7][C:6]=1[O:19][CH3:20])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 22894817HCID 22894817, compound

Product 1

HCID 15875321HCID 15875321, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

1.0 g (3.6 mmol) diacetate 13 is dissolved in 17 ml EtOH and hydrogenated over PtO2. The catalyst is removed by filtration over Celite and the solvent is evaporated. Flash chromatography of the crude product gave 0.83 g (82% by weight) of compound 14 in the form of a yellowish oil having the following 1H NMR (CDCl3) values: 0.81 (d, J=7.0, CH3); 0.98 (d, J=7.0, CH3); 1.98-2.15 (m, 1H, CH); 2.08 (s, CH3); 2.30 (s, CH3); 3.82 (s, OCH3); 5.46 (d, J=7.0, CH); 6.84-7.02 (m, 3 aromatic H). MS 280 (8, [M+]), 238 (38), 195 (56), 153 (100), 43 (68).

Workup

  1. customThe catalyst is removed by filtration over Celite
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-21786c9d45004ca78b699179fa42a1c6
Source dataset
uspto-grants-2001_03
Patent number
US06203839B1

Reaction notes

Loading…