Water → [2-(Trifluoromethyl)-1H-indol-3-yl]methanol

HRID 231836

Reaction equation

HRID 231836 reaction equation
[BH4-].[K+].[F:3][C:4]([F:17])([F:16])[C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH:14]=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2.O1CCCC1.O>CCOCC>[F:17][C:4]([F:3])([F:16])[C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:14][OH:15])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 4192641Potassium borohydrideHCID 200321282-trifluoromethyl-3-formyl-(1H)-indole

Product 1

HCID 20032113[2-(Trifluoromethyl)-1H-indol-3-yl]methanolYield 64.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2 g of potassium borohydride were added in small fractions at +5° C. to a solution of 4.6 g of the product of Step A, 150 ml of tetrahydrofuran and 30 ml of water and the mixture was stirred for one hour. The mixture was allowed to return to ambient temperature and the tetrahydrofuran was eliminated under reduced pressure. The resulting mixture was diluted with ether, washed with water, dried and concentrated under reduced pressure. The residue was chromatographed over silica (eluent: hexaneethyl acetate 7-3) to obtain 3 g of 2-trifluoromethyl-(1H)-indol-3-yl methanol melting at 106° C.

Workup

  1. customto return to ambient temperature
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed over silica (eluent: hexaneethyl acetate 7-3)

Sources & evidence

ORD record
ord-ad967951fb5a48f7bfe9f3319054f3fa
Source dataset
uspto-grants-1989_07
Patent number
US04849443

Linked notes

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