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

HRID 231838

Reaktionsgleichung

Reaktionsgleichung von HRID 231838
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 223920981-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl methanolAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-656990a9fdd24678bf66af77d0e0c965
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04849443

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