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Ethylene Glycol → 1h-Indole-1-carboxylic acid,5-(2-methyl-1,3-dioxolan-2-yl)-,1,1-dimethylethyl ester

HRID 2078696
Notes
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Reaction equation

HRID 2078696 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](=[O:19])[CH3:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20](O)[CH2:21][OH:22].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3([CH3:18])[O:22][CH2:21][CH2:20][O:19]3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 57637401tert-Butyl 5-acetyl-1H-indole-1-carboxylate2×

Product 1

HCID 576373041h-Indole-1-carboxylic acid,5-(2-methyl-1,3-dioxolan-2-yl)-,1,1-dimethylethyl ester

Reagents, catalysts & solvents

1
HCID 241BenzeneSolvent

Procedure

A mixture of 5-acetyl-indole-1-carboxylic acid tert-butyl ester [4.85 g, 18.70 mmol, Intermediate (18)], ethylene glycol (5.0 g), pyridinium p-toluenesulfonate (100 mg) in benzene (35 mL) is refluxed under N2 with a Dean-Stark trap for 24 hours. To this resulting dark reaction mixture is added solid NaHCO3 (2.5 g). After stirring for 15 minutes, it is filtered under suction and washed three times with ethyl acetate (30 mL). The filtrate is washed twice with water (10 mL) and dried over sodium sulfate. The crude is chromatographed on 10 g silica gel cartridge (heptane then 10% ethyl acetate in heptane) afforded 5-(2-methyl-[1,3]dioxolan-2-yl)-indole-1-carboxylic acid tert-butyl ester [Intermediate (19)] as colorless oil; 1H NMR (CDCl3): δ 8.128 (1H, d), 7.706 (1H, s), 7.625 (1H), 7.475 (1H, dd), 6.591 (1H, d), 4.106 (2H, m), 3.843 (2H, m), 1.742 (3H, s), 1.703 (9H, s); LC/MS: 304 (M+H).

Workup

  1. temperatureis refluxed under N2 with a Dean-Stark trap for 24 hours
  2. customTo this resulting dark reaction mixture
  3. filtrationit is filtered under suction
  4. washwashed three times with ethyl acetate (30 mL)
  5. washThe filtrate is washed twice with water (10 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe crude is chromatographed on 10 g silica gel cartridge (heptane

Sources & evidence

ORD record
ord-fdfd7409e9f04fe291d44d943669075a
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928231B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes