Ethanol → HCID 117780653, compound

HRID 2206528Notes

Reaction equation

HRID 2206528 reaction equation
[CH3:1][C:2]1[N:3]([CH:15]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH3:16])[C:4]2[C:9]([C:10]=1[C:11]([O:13]C)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(O)C.[OH-].[Na+]>>[CH3:1][C:2]1[N:3]([CH:15]([CH:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[CH3:16])[C:4]2[C:9]([C:10]=1[C:11]([OH:13])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 117804446HCID 117804446, compound

Product 1

HCID 117780653HCID 117780653, compoundYield 93.2%

Procedure

A 1 L round bottom flask was charged with a magnetic stir bar, (R or S)-methyl 2-methyl-1-(1-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-indole-3-carboxylate (11.60 g, 38.5 mmol), ethanol (96 ml, 38.5 mmol), and 6 N aqueous NaOH (64.1 ml, 385 mmol). The flask was fitted with a reflux condenser and heated to reflux for 6 h before being allowed to cool to rt. The volatiles were removed in vacuo and the resulting mixture was poured into 10% HCl (˜300 mL). A precipitate formed which was collected via vacuum filtration using a Buchner funnel. The filter cake was rinsed with an additional portion of water (˜200 mL), collected, and dried under vacuum to afford the title compound (10.87 g, 35.9 mmol, 93% yield) as an off-white solid.

Workup

  1. additionA 1 L round bottom flask was charged with a magnetic stir bar
  2. customThe flask was fitted with a reflux condenser
  3. temperatureheated
  4. temperatureto reflux for 6 h
  5. customThe volatiles were removed in vacuo
  6. additionthe resulting mixture was poured into 10% HCl (˜300 mL)
  7. customA precipitate formed which
  8. filtrationwas collected via vacuum filtration
  9. washThe filter cake was rinsed with an additional portion of water (˜200 mL)
  10. customcollected
  11. customdried under vacuum

Sources & evidence

ORD record
ord-a107920ca4024f419df065dbe1b8d0b5
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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