4-Hydroxybenzaldehyde → tert-Butyl 4-(4-formylphenoxy)piperidine-1-carboxylate

HRID 1434568Notes

Reaction equation

HRID 1434568 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20](O)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CCCCCC.C(OCC)(=O)C>O1CCCC1>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 21226206Ethyl acetate hexane

Product 1

HCID 22632605tert-Butyl 4-(4-formylphenoxy)piperidine-1-carboxylateYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxybenzaldehyde (2.0 g, 16.4 mmol) was dissolved in tetrahydrofuran (20 ml) and treated with 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (4.1 g, 20.5 mmol) and by column chromatography on silica eluting with 4-1 hexane-ethyl acetate to afford the title compound as a colourless viscous oil (3.8 g)

Sources & evidence

ORD record
ord-c162c759661f46d988bcb4b9cf3c6c8f
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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