Tetrahydrofuran → HCID 21099157, compound

HRID 1095541Notes

Reaction equation

HRID 1095541 reaction equation
B.C1COCC1.C([O:9][C:10](=O)[CH2:11][C:12]1(O)[C:20]2[C:15](=[CH:16][C:17]([Cl:22])=[C:18]([Cl:21])[CH:19]=2)[NH:14][C:13]1=O)C.O1CCCC1.C(OCC)(=O)C>O>[Cl:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[Cl:22])[NH:14][CH:13]=[C:12]2[CH2:11][CH2:10][OH:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 2723981Borane;tetrahydrofuranHCID 57475154HCID 57475154, compound

Product 1

HCID 21099157HCID 21099157, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 M borane/THF solution (28.0 ml. 28.0 mmol) was added to a solution of the (5,6-dichloro-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid ethyl ester just prepared (2.13 g, 7.0 mmol), in abs. tetrahydrofuran (15 ml), in an ice bath in the course of 15 min. The reaction mixture was stirred at room temperature for 57 h and, for working up, was added to a mixture of ethyl acetate (50 ml) and water (50 ml), while stirring. The phases were separated and the aqueous phase was extracted with ethyl acetate (2×30 ml). The organic phases were combined, dried and concentrated. The crude indole was obtained as a yellow oil (1.9 g) by this procedure. Purification by chromatography [silica gel G (80 g); ethyl acetate/cyclohexane 1:2 (2 l)] gave the desired 2-(5,6-dichloro-1H-indol-3-yl)ethanol (Ind-83) as a beige-coloured solid in a yield of 60% (0.96 g) (m.p. 65-67° C.).

Workup

  1. customjust prepared (2.13 g, 7.0 mmol)
  2. customin the course of 15 min
  3. stirringwhile stirring
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (2×30 ml)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8d21bca660c649ddaec50cb54f4baa67
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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