Tetrahydrofuran → 1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl methanol

HRID 231838

Reaction equation

HRID 231838 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[C:5]1[C:15]([F:18])([F:17])[F:16])[C:2]#[CH:3].O1CCCC1.[BH4-].[K+]>O>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][OH:14])=[C:5]1[C:15]([F:18])([F:16])[F:17])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4192641Potassium borohydrideHCID 200321241-(2-propynyl)-2-trifluoromethyl-3-formyl-(1H)-indol

Product 1

HCID 223920981-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl methanolYield 100.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.54 g of 1-(2-propynyl)-2-trifluoromethyl-3-formyl-(1H)-indol, 120 ml of tetrahydrofuran and 20 ml of water were mixed together at +5° and 2 g of potassium borohydride were added in small fractions. The mixture was concentrated to a small volume by distillation under reduced pressure and ethyl ether was added. The organic phase was washed with salted water and concentrated to dryness by distillation under reduced pressure to obtain 5.6 g of 1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl methanol melting at 90° C.

Workup

  1. concentrationThe mixture was concentrated to a small volume by distillation under reduced pressure and ethyl ether
  2. additionwas added
  3. washThe organic phase was washed with salted water
  4. concentrationconcentrated to dryness by distillation under reduced pressure

Sources & evidence

ORD record
ord-656990a9fdd24678bf66af77d0e0c965
Source dataset
uspto-grants-1989_07
Patent number
US04849443

Linked notes

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