Potassium Hydroxide → HCID 68596887, compound

HRID 884640Notes

Reaction equation

HRID 884640 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][C:5]=1[CH3:12].[C:13]([C:16]1[CH:36]=[CH:35][C:19]([O:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:18][C:17]=1[CH3:37])(=[O:15])[CH3:14]>CCO>[OH:3][C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[CH:14]/[C:13]([C:16]2[CH:36]=[CH:35][C:19]([O:20][CH2:21][CH:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:26][CH2:27]3)=[CH:18][C:17]=2[CH3:37])=[O:15])=[CH:6][C:5]=1[CH3:12]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 68596593HCID 68596593, compound

Product 1

HCID 68596887HCID 68596887, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a round bottomed flask was added EtOH (10 mL) and potassium hydroxide (507 mg, 9.05 mmol). The mixture was stirred until homogeneous before adding commercially available 4-hydroxy-3-methyl benzaldehyde (247 mg, 1.81 mmol) and tert-butyl 4-((4-acetyl-3-methylphenoxy)methyl)piperidine-1-carboxylate (630 mg, 1.81 mmol). The reaction was heated to 80° C. for 5 h, cooled to rt, and concentrated via rotary evaporation. The product was dry-loaded onto a silica gel column and purified through flash chromatography (1:1 EtOAc:Hexanes) to afford (E)-tert-butyl 4-((4-(3-(4-hydroxy-3-methylphenyl)acryloyl)-3-methylphenoxy)methyl)piperidine-1-carboxylate (400 mg, 47% yield).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated via rotary evaporation
  3. custompurified through flash chromatography (1:1 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-07fb6680840a40a8aec5aefd9c2e7bd9
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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