Hexane → 1-Benzyloxycarbonyl-5-chloro-3-chloromethylindole

HRID 564848Notes

Reaction equation

HRID 564848 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[C:13]([CH2:21]O)=[CH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O.CCCCCC>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[C:13]([CH2:21][Cl:25])=[CH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 184739211-Benzyloxycarbonyl-5-chloro-3-hydroxymethylindole

Product 1

HCID 184739631-Benzyloxycarbonyl-5-chloro-3-chloromethylindole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyloxycarbonyl-5-chloro-3-hydroxymethylindole (1.45 g) in dichloromethane (23 ml) was added thionylchloride (0.797 μl) at −78° C. After the mixture was stirred for 1.5 hours at room temperature, the reaction mixture was concentrated under the reduced pressure to give a residue. Hexane was added to the residue. 1-benzyloxycarbonyl-5-chloro-3-chloromethylindole (1.43 g) was obtained as a crystal.

Workup

  1. concentrationthe reaction mixture was concentrated under the reduced pressure
  2. customto give a residue

Sources & evidence

ORD record
ord-b0bfb1c87b064a4c936f2d06778c99b7
Source dataset
uspto-grants-2001_01
Patent number
US06169102A

Reaction notes

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