HCID 11736760, compound → HCID 15875322, compound

HRID 1532532Notes

Reaction equation

HRID 1532532 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 1NMR (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-cb25a0061f354be6958d0ccc243165b9
Source dataset
uspto-grants-2001_03
Patent number
US06203839B1

Reaction notes

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