Sodium Hydroxide → 1H-Indole-6-carboxaldehyde

HRID 1362050Notes

Reaction equation

HRID 1362050 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=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 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dess-Martin periodinane (1.53 g, 2.6 mmol) was dissolved into methylene chloride (15 mL). Indol-6-yl-methanol (500 mg, 3.4 mmol) in methylene chloride (12 mL) was added and the mixture was stirred for 1 hr. Sodium hydroxide (5 mL of 1 N solution) was added and the reaction was stirred for 15 min. The organic layer was separated and washed with H2O (5 mL), brine (5 mL), dried over MgSO4 and concentrated to afford the title compound as a brown solid (275 mg, 56%). 1H NMR (300 MHz, DMSO-d6) δ 11.7 (s, 1H), 9.98 (s, 1H), 7.97 (s, 1H), 7.70-7.65 (m, 2H), 7.52 (dd, J=8.2, 1.4 Hz, 1H), 6.57-6.5 (m, 1H).

Workup

  1. stirringthe reaction was stirred for 15 min
  2. customThe organic layer was separated
  3. washwashed with H2O (5 mL), brine (5 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb42b14b7a40475493d6e5adc33a45ef
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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