HCID 11736760, compound → HCID 15875322, compound

HRID 1633818Notes

Reaction equation

HRID 1633818 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])[CH2:12][CH:13]=[CH2:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>CCO.O=[Pt]=O>[C:16]([O:15][CH:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:10][CH:9]=1)[CH2:12][CH2:13][CH3:14])(=[O:18])[CH3:17]

Participants

4

Reactant 1

HCID 11736760HCID 11736760, compound

Product 1

HCID 15875322HCID 15875322, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

1.0 g (4 mmol) diacetate 9 is dissolved in 19 ml EtOH and hydrogentated over 50 mg PtO2. The catalyst is removed by filtration over Celite and the solvent is evaporated. Flash chromatography of the crude product gave 0.92 g (91% by weight) of compound 15 in the form of a yellowish oil having the following 1H NMR (CDCl3) values: 0.92 (t, J=7.0, CH3); 1.15-1.45 (m, 2H, CH2); 1.62-2.00 (m, 2H, CH2); 2.05 (s, CH3); 2.30 (s, CH3); 5.74 (t, J=7.0, CH); 7.06 (d, J=9.0, 2 aromatic H); 7.34 (d, J=9.0, 2 aromatic H). MS: 250 (2, [M+]), 208 (19), 165 (32), 123 (68), 43 (100).

Workup

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

Sources & evidence

ORD record
ord-08ff1c3c56c54298afb41e6451eb653a
Source dataset
uspto-grants-2003_01
Patent number
US06504048B1

Reaction notes

Loading…