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Potassium Carbonate → Diethyl 2-(indol-4-yloxy)malonate

HRID 16566
Notes
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Reaction equation

HRID 16566 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C(=O)([O-])[O-].[K+].[K+].[Br:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[Br:17][C:18]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20].[NH:6]1[C:7]2[C:3](=[C:2]([O:1][CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 754211H-indol-4-ol

Product 2

HCID 11608989Diethyl 2-(indol-4-yloxy)malonateYield 34%HCID 11639270Diethyl 2-bromo-2-(indol-4-yloxy)malonateYield 13%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent
2×

Procedure

A solution of 4-hydroxyindole (266 mg, 2 mmol) in acetone (20 mL) was cooled to 0° C. under nitrogen and anhydrous potassium carbonate (414 mg, 3 mmol) was added. A solution of freshly distilled pure diethyl bromomalonate (574 mg, 2.4 mmol) in acetone (20 mL) was added dropwise and the mixture was stirred at room temperature overnight. Work up and flash chromatography as above afforded 7 (101 mg, 13%) and 8 (199 mg, 34%).

Sources & evidence

ORD record
ord-0c9a0cdfc8304382bf05447a70154c88
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737169B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes