Diethyl Ether → Indole-4-carboxaldehyde

HRID 2097130Notes

Reaction equation

HRID 2097130 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[NH:23]1[C:31]2[C:26](=[C:27]([CH2:32][OH:33])[CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1.[OH-].[Na+].CCOCC>C(Cl)Cl>[NH:23]1[C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([CH:32]=[O:33])[C:26]=2[CH:25]=[CH:24]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 27734571H-indol-4-ylmethanol

Product 1

HCID 333703Indole-4-carboxaldehydeYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dess-Martin periodane (1.04 g, 2.46 mmol) was dissolved into anhydrous CH2Cl2 (10 ml). (1H-Indol-4-yl)-methanol (449 mg, 3.07 mmol) in anhydrous CH2Cl2 (10 ml) was added and the mixture was stirred for 1 h. Sodium hydroxide (50 ml of 1N solution) and ether (50 ml) were added and the reaction was stirred for 30 min. The organic layer was separated and washed with water (10 ml), brine (10 ml), dried over MgSO4, filtered and concentrated to a thick brown oil. Purification by column chromatography (silica gel, gradient elution of 2% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2) gave 1H-indole-4-carbaldehyde (235 mg, 53%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 11.59 (bs, 1H), 10.18 (s, 1H), 7.78-7.75 (m, 1H), 7.66-7.60 (m, 2H), 7.33-7.28 (m, 1H), 7.08 (d, J=3.0 Hz, 1H).

Workup

  1. stirringthe reaction was stirred for 30 min
  2. customThe organic layer was separated
  3. washwashed with water (10 ml), brine (10 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a thick brown oil
  7. customPurification
  8. washby column chromatography (silica gel, gradient elution of 2% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f43ff1ce406e436e9d33e112e2cb6de1
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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