Diethyl Ether → 2-(5-Bromo-1H-indol-1-yl)ethanol

HRID 1945303Notes

Reaction equation

HRID 1945303 reaction equation
CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21](OC)=[O:22])[CH:15]=[CH:14]2.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].CCOCC>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][CH2:21][OH:22])[CH:15]=[CH:14]2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 43152068HCID 43152068, compound

Product 1

HCID 106576502-(5-Bromo-1H-indol-1-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIBAL-H (1 M in hexanes) (6.1 mL, 6.1 mmol) was added to a 0° C. solution of methyl (5-bromo-1H-indol-1-yl)acetate (660 mg, 2.46 mmol) in anhydrous THF (12 mL). The reaction was warmed to ambient temperature and maintained for 1 h. The reaction mixture was poured into saturated aqueous Rochelle's salt (25 mL) and Et2O (25 mL). The mixture was stirred vigorously for 30 min. The layers were separated and the aqueous phase was extracted with Et2O. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated to afford the desired product as a yellow oil.

Workup

  1. temperaturemaintained for 1 h
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with Et2O
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ff3822d0225e430dadfdd831dc0d7e8f
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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