Iodoethane → 1-Ethyl-1H-indole-3-carbaldehyde

HRID 1843918Notes

Reaction equation

HRID 1843918 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4]1.[CH2:14](I)[CH3:15].C(OC(=O)C)C>CN(C=O)C.CCCCCC>[CH2:14]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4]1)[CH3:15]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 5990901-Ethyl-1H-indole-3-carbaldehydeYield 87.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

NaH (1.51 g, 37.891 mmol) was added to a solution of 1H-indole-3-carbaldehyde (I-38a: 5 g, 34.447 mmol) in dry DMF (40 mL) at 0° C. and the reaction mixture was stirred for 5 minutes. This was followed by dropwise addition of ethyl iodide (6.45 g, 41.336 mmol) over a period of 5 mins and stirring was continued for a further 1 hr. The reaction was monitored by TLC (40% ethylacetate in hexane). The reaction mixture was quenched with chilled water and filtered. The residue was washed with water and dried to afford 5.2 g of the product (86% yield).

Workup

  1. stirringstirring
  2. waitwas continued for a further 1 hr
  3. customThe reaction mixture was quenched with chilled water
  4. filtrationfiltered
  5. washThe residue was washed with water
  6. customdried

Sources & evidence

ORD record
ord-0e8bd8e8618247c19bd171c643abee2f
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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