HCID 22894817, compound → HCID 15875321, compound

HRID 1016708Notes

Reaction equation

HRID 1016708 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-c1fad5f88369437cabc50b3d8689e0e4
Source dataset
uspto-grants-2002_11
Patent number
US06476252B1

Reaction notes

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