Lithium borohydride → HCID 69199097, compound

HRID 268651Notes

Reaction equation

HRID 268651 reaction equation
C([O:3][C:4](=O)[C:5]([C:7]1[C:15]2[C:10](=[C:11]([CH2:17][CH3:18])[CH:12]=[C:13]([Br:16])[CH:14]=2)[NH:9][CH:8]=1)=O)C.[BH4-].[Li+]>O1CCCC1>[Br:16][C:13]1[CH:14]=[C:15]2[C:10](=[C:11]([CH2:17][CH3:18])[CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:5][CH2:4][OH:3]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69197998HCID 69197998, compound

Product 1

HCID 69199097HCID 69199097, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of (5-bromo-7-ethyl-1H-indol-3-yl)-oxo-acetic acid ethyl ester (1.55 g, 4.8 mmol) in tetrahydrofuran at room temperature under nitrogen was dropped a 2.0 M solution of lithium borohydride in tetrahydrofuran. The reaction mixture was heated at 90° C. oil bath for 5 hours. After cooling to room temperature, it was quenched with 5% hydrochloric acid solution until the excess lithium borohydride was destroyed. To the mixture was added saturated sodium bicarbonate solution and extracted with ethyl acetate. Extracts were dried over magnesium sulfate and concentrated under reduced pressure to give the crude product of 2-(5-bromo-7-ethyl-1H-indol-3-yl)-ethanol, which went to the next reaction without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. customit was quenched with 5% hydrochloric acid solution until the excess lithium borohydride
  3. customwas destroyed
  4. additionTo the mixture was added saturated sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. dry with materialExtracts were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1a32b3ddeae44238f272f26f4d89a3e
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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