Ethanol → ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylate

HRID 519275Notes

Reaction equation

HRID 519275 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[NH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)=[O:4].[O-][CH2:17][CH3:18].[Na+].C([OH:22])C>>[NH:6]1[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=[C:5]1[C:3]([O:4][CH2:17][CH3:18])=[O:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 670161542,2,2-trichloro-1-(4,5,6,7-tetrahydro-1H-indol-2-yl)ethanone

Product 1

HCID 300702ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylateYield 100%

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was purged with nitrogen and charged with 2,2,2-trichloro-1-(4,5,6,7-tetrahydro-1H-indol-2-yl)ethanone 104f (6.50 g, 24.8 mmol), sodium ethoxide (17.0 mg, 0.25 mmol) and ethanol (40 mL). The solution was stirred at room temperature for 1 h. After that time, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography to afford a 100% yield (4.80 g) of ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylate 104g as a brown solid: mp 70-72° C.; 1H NMR (300 MHz, CDCl3) δ 9.08 (s, 1H), 6.75 (s, 1H), 4.25 (q, 2H, J=7.2 Hz), 2.65 (t, 2H, J=6.0 Hz), 2.56 (t, 2H, J=6.0 Hz), 1.85 (m, 4H), 1.28 (t, 3H, J=7.2 Hz); MS (ESI+) m/z 194.1 (M+H)

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. customwas purged with nitrogen
  3. concentrationAfter that time, the reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5418c604c6514fe5874fddb13f3b9024
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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