Lithium tri-s-butylborohydride → HCID 18679504, compound

HRID 1633657Notes

Reaction equation

HRID 1633657 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:30]3[C:25](=[CH:26][C:27]([O:31]C)=[CH:28][CH:29]=3)[CH:24]=[CH:23]2)=[CH:18][CH:17]=1>C1COCC1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:30]3[C:25](=[CH:26][C:27]([OH:31])=[CH:28][CH:29]=3)[CH:24]=[CH:23]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 18679488HCID 18679488, compound

Product 1

HCID 18679504HCID 18679504, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To 140 ml (140 mmol) 1M L-selectride in THF (Lithium-tri-sec-butylborohydride), 14.9 g (50 mmol) 1-(4-Bromo-phenyl)-5-methoxy-1H-indole were added slowly in small portions at RT. The mixture was stirred at 75° C. for 60 h, concentrated and dissolved in ether and water. The organic phase was washed with water and dried over Na2SO4. Trituration with cyclohexane yielded 13.9 g (96%) 1-(4-Bromo-phenyl)-1H-indol-5-ol as grey solid, MS: 287 (MH+).

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in ether
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e5f26b2195344ce391faf306a50ffedc
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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