Acetic acid methanol → HCID 131715536, compound

HRID 1252745Notes

Reaction equation

HRID 1252745 reaction equation
C(O[CH:5]1[O:11][C@H:10]([CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@:8](CC2C=CC=CC=2)([OH:9])[C@:6]1([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[OH:7])(=O)C.CO.[CH3:37][C:38]([OH:40])=[O:39]>[Pd].N1C=CC=CC=1>[C:38]([O:40][C@H:5]1[O:11][C@H:10]([CH2:8][OH:9])[C@@H:12]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@:6]1([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[OH:7])(=[O:39])[CH3:37]

Participants

5

Reactant 2

HCID 10129899Acetic acid methanolHCID 131715537HCID 131715537, compound

Product 1

HCID 131715536HCID 131715536, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

To a solution of acetate (V) (20.6 g, 4.46 mmol) in a 1:1 solution of MeOH/HOAc (100 ml) was added 2.0 g of 10% Pd/C and 82 μl of pyridine (0.4%). The solution was shaken on a Parr apparatus under 50 psig of H2. After 24 h the solution was filtered and concentrated, and the residue was purified on a Waters Prep-500 HPLC (EtOAc/hexane, 22/78) to yield 6.4 g of a light yellow oil (39%), homogeneous by TLC. This reaction routinely gave yields of 35-40%. The point at which the reaction is removed from the hydrogenator is determined by when the selectively reduced compound appears greatest by TLC analysis. 1H NMR (CDCl3)δ: 7.3 (s, 10H), 6.2 (br s, 1H), 3.6-4.7 (m, 9H), 2.10 (s, 3H). 13C NMR (CDCl3) δ: 169.9, 137.5, 137.1, 128.5 (4C), 128.0 (4C), 127.7 (2C), 100.4 (αC-1), 86.8, 84.6, 82.8, 72.4, 72.1, 62.1, 21.2 Elemental Analysis: Calculated for C21H24O6 : C, 67.73; H, 6.50. Found: C, 67.49; H, 6.50.

Workup

  1. filtrationAfter 24 h the solution was filtered
  2. concentrationconcentrated
  3. customthe residue was purified on a Waters Prep-500 HPLC (EtOAc/hexane, 22/78)

Sources & evidence

ORD record
ord-1e5beadcee794531ab0f80c456173db6
Source dataset
uspto-grants-1988_05
Patent number
US04745185

Reaction notes

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