Sodium Hydroxide → 1H-Indole-6-carboxaldehyde

HRID 2097123Notes

Reaction equation

HRID 2097123 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](=[CH:27][CH:28]=[C:29]([CH2:32][OH:33])[CH:30]=2)[CH:25]=[CH:24]1.[OH-].[Na+]>C(Cl)Cl>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH:32]=[O:33])[CH:30]=2)[CH:25]=[CH:24]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 27734596-Hydroxymethylindole

Product 1

HCID 27734351H-Indole-6-carboxaldehydeYield 24.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dess-Martin periodane (2.56 g, 6.04 mmol) was dissolved into anhydrous CH2Cl2 (25 ml). (1H-Indol-6-yl)-methanol (883 mg, 6.04 mmol) in anhydrous CH2Cl2 (20 ml) was added and the mixture was stirred for 1 h. Aqueous sodium hydroxide (12 ml of 1N solution) was 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-6-carbaldehyde (212 mg, 24%) as a brown solid: 1H NMR (300 MHz, DMSO-d6) δ 11.67 (bs, 1H), 9.99 (s, 1H), 7.97 (s, 1H), 7.70-7.65 (m, 2H), 7.54-7.50 (m, 1H), 6.59-5.54 (m, 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-6abf862921e549e38a121d262e044449
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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