1,2-Dichloroethane → HCID 18182189, compound

HRID 1359407Notes

Reaction equation

HRID 1359407 reaction equation
[B-]C#N.[Na+].[C:5]([C:7]1[CH:11]=[CH:10][S:9][C:8]=1[CH:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[CH:6].ClCCCl>[I-].[Zn+2].[I-].C(OCC)C>[CH2:12]([C:8]1[S:9][CH:10]=[CH:11][C:7]=1[C:5]#[CH:6])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 18182446HCID 18182446, compoundHCID 20587905Sodium cyanoborohydride [MI]

Product 1

HCID 18182189HCID 18182189, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

201 mg of sodium cyanotrihydroborate was added to a mixture of 85.7 mg of 3-ethynyl-2-(α-hydroxybenzyl)thiophene, 192 mg of zinc iodide and 1.5 ml of 1,2-dichloroethane at room temperature, followed by stirring at the same temperature overnight. 5 ml of diethyl ether was added to the reaction solution, followed by filtering through Celite. After the solvent was removed, the residue was subjected to silica gel column chromatography using 2% ethyl acetate/hexane, to give 45.2 mg of the target compound.

Workup

  1. filtrationby filtering through Celite
  2. customAfter the solvent was removed

Sources & evidence

ORD record
ord-009d5768bf12441fbaf247371d2d7648
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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