Ethyl Acetate → HCID 86753105, compound

HRID 2393575Notes

Reaction equation

HRID 2393575 reaction equation
[CH:1]1([C@@H:7]([OH:20])/[CH:8]=[CH:9]/[C@@H:10]2[C@@H:17]3[C@@H:13]([O:14][C:15](=[O:18])[CH2:16]3)[CH2:12][C@H:11]2[OH:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OCC)(=O)C>[Pd].C(Cl)Cl>[CH:1]1([C@@H:7]([OH:20])[CH2:8][CH2:9][C@@H:10]2[C@@H:17]3[C@@H:13]([O:14][C:15](=[O:18])[CH2:16]3)[CH2:12][C@H:11]2[OH:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 86753104HCID 86753104, compound

Product 1

HCID 86753105HCID 86753105, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 43 (5.3 g, 18.9 mmol), 10% w/w Pd/C (320 mg), ethyl acetate (30 mL), and CH2Cl2 (10 mL) was hydrogenated in a Parr hydrogenation apparatus for 3 h at 45 psi. The mixture was filtered through Celite and concentrated, and the residue was chromatographed on silica gel (ethyl acetate) to afford 44 (4.3 g, 80%). 13C NMR (CDCl3) δ 177.64 (C), 83.87 (CH), 77.21 (CH), 76.02 (CH), 53.45 (CH), 43.84 (CH), 42.96 (CH), 40.46 (CH2), 35.88 (CH), 31.37 (CH2), 29.23 (CH2), 29.10 (CH2), 27.85 (CH2), 26.41 (CH), 26.22 (CH2), 26.08 (CH2).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customthe residue was chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-2a1ce50e169f4db4a2e071e7793b0c9c
Source dataset
uspto-grants-1998_09
Patent number
US05807892

Reaction notes

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