Dichloromethane → (2-tert-butyl-5-nitro-1H-indol-7-yl)methanol

HRID 1908439Notes

Reaction equation

HRID 1908439 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=2[C:17](OC)=[O:18])([CH3:4])([CH3:3])[CH3:2].ClCCl.CC(C[AlH]CC(C)C)C>O>[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=2[CH2:17][OH:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14487Diisobutylaluminum hydrideHCID 53436897Methyl 2-tert-butyl-5-nitro-1H-indole-7-carboxylate

Product 1

HCID 59129235(2-tert-butyl-5-nitro-1H-indol-7-yl)methanolYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-tert-butyl-5-nitro-1H-indole-7-carboxylate (6.15 g, 22.3 mmol) and dichloromethane (30 ml) was added DIBAL-H (1.0 M, 20 mL, 20 mmol) at 78° C. The mixture was stirred for 1 h before water (10 mL) was added slowly. The resulting mixture was extracted with EtOAc (120 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give (2-tert-butyl-5-nitro-1H-indol-7-yl)methanol (4.0 g, 73%), which was used in the next step directly.

Workup

  1. additionwas added slowly
  2. extractionThe resulting mixture was extracted with EtOAc (120 mL×3)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-2678f9b7c96442448fddf16d9a86ac89
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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