Diethyl Ether → HCID 17985621, compound

HRID 557225Notes

Reaction equation

HRID 557225 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)=[O:2].C[Li].[CH2:14](OCC)C.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH:1]([OH:2])[CH3:14])[CH:8]=[CH:9]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 2734629Indole-7-carboxaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 17985621HCID 17985621, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 7-formylindole (1.0 g, 6.89 mmol) in anhydrous tetrahydrofuran (15 ml) dropwise to a solution of 1.4M methyllithium in diethyl ether (12.2 ml, 17.1 mmol) at −78° C. After 15 minutes add saturated aqueous sodium bicarbonate (15 ml). Dilute with 1:1 ethyl acetate:diethyl ether, wash with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride, dry over magnesium sulfate, and concentrate under reduced pressure to provide desired compound (1.05 g, 94%) as a white solid.

Workup

  1. washdiethyl ether, wash with saturated aqueous sodium bicarbonate
  2. dry with materialdry over magnesium sulfate
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-19d3e285f3fa4458a23b033ba713b45c
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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