HCID 22894817, compound → HCID 15875321, compound

HRID 1633817Notes

Reaction equation

HRID 1633817 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-9532a2348d65495484a88ea909a0d9ff
Source dataset
uspto-grants-2003_01
Patent number
US06504048B1

Reaction notes

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