Methanol → HCID 117876653, compound

HRID 1501526Notes

Reaction equation

HRID 1501526 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:25][CH3:26])=[CH:5][C:6]2[O:10][C:9]([C:11]([CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH2:12])=[CH:8][C:7]=2[CH:24]=1.[CH3:27]O>[Pd]>[CH3:1][O:2][C:3]1[C:4]([O:25][CH3:26])=[CH:5][C:6]2[O:10][C:9]([CH:11]([CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:21])[CH3:22])[CH2:12][CH3:27])=[CH:8][C:7]=2[CH:24]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 117876177HCID 117876177, compound

Product 1

HCID 117876653HCID 117876653, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of compound A4 (0.7 g 1.9 mmol) in MeOH was added 10 Mol % Pd/C and reaction was shacked at 40 psi pressure for 0.5 hrs. After completion of the reaction (monitored by TLC) filtered the reaction mixture and evaporated the methanol completely. Chromatography of the residue on silica gel (3% EtOAc/Hexanes) afforded the compound A5 (0.633 g) in 90% yield colorless liquid: 1H NMR (500 MHz, CDCl3) δ 7.04 (s, 1H), 6.98 (s, 1H), 6.294 (s, 1H), 5.15-5.12 (m, 4H), 3.940 (s, 6H), 2.94-2.91 (m, 1H), 2.10-1.98 (m, 4H), 1.87-1.82 (m, 2H), 1.74 (s, 3H), 1.634 (s, 3H), 1.59 (s, 3H), 1.34-1.32 (d, 3H), ppm. Mass: ESI [M+Na]+: 356.24; Elemental anal. calcd. for C23H32O3; C, 77.49; H, 9.05. found C, 77.49; H, 9.05.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. filtrationfiltered the reaction mixture
  3. customevaporated the methanol completely

Sources & evidence

ORD record
ord-48afa5e3250e4db7adab2a65196d0851
Source dataset
uspto-grants-2015_12
Patent number
US09206201B2

Reaction notes

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