Sodium Hydroxide → 2-(3-Benzyloxy-5-hydroxyphenyl)-4-methyl-pent-4-enoic acid methyl ester

HRID 426338Notes

Reaction equation

HRID 426338 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23]CC2C=CC=CC=2)[CH:10]=1)[CH2:5][C:6]([CH3:8])=[CH2:7].[OH-].[Na+]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:10]=[C:11]([OH:23])[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[CH2:5][C:6]([CH3:8])=[CH2:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 577550392-(3,5-Bis-benzyloxyphenyl)-4-methyl-pent-4-enoic acid methyl ester

Product 1

HCID 577549962-(3-Benzyloxy-5-hydroxyphenyl)-4-methyl-pent-4-enoic acid methyl esterYield 67.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (Aldrich cat no 205699, 0.55 g) was added to a stirred solution of 2-(3,5-bis-benzyloxyphenyl)-4-methyl-pent-4-enoic acid methyl ester (14.1 g, 33.8 mmol) and NaOH (1.50 g, 37.5 mmol) in MeOH (180 mL) at room temperature. Stirring was continued for 1 h under H2 (1 atm.) then the mixture was filtered through Celite, concentrated in vacuo, suspended in water (100 mL) and adjusted to pH 2 with 1M HCl. The mixture was extracted with EtOAc (2×180 mL); the combined organic layer was washed with brine (50 mL), dried (MgSO4), concentrated in vacuo and purified by flash chromatography (silica, 0-30% EtOAc in petroleum ether) to give the title product as a yellow oil (7.40 g, 67%) 1H-NMR (400 MHz, CDCl3): δ 7.41-7.25 (m, 5H), 6.54 (s, 1H), 6.43 (s, 1H), 6.38 (s, 1H), 5.01 (s, 3H), 4.74 (s, 1H), 4.67 (s, 1H), 3.70 (t, 1H), 3.65 (s, 3H), 2.78 (dd, 1H), 2.38 (dd, 1H), 1.71 (s, 3H); Mass spectrum (ESI, m/z) 325 (M−1)

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. extractionThe mixture was extracted with EtOAc (2×180 mL)
  4. washthe combined organic layer was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (silica, 0-30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-e0f839ebe3164adaaa5a5d7667bcee26
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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