Chloromethyl Methyl Ether → HCID 14277639, compound

HRID 1200015Notes

Reaction equation

HRID 1200015 reaction equation
[OH:1][C:2]1[C:3]2[CH:16]=[CH:15][N:14]=[CH:13][C:4]=2[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[Na+].[CH3:19][O:20][CH2:21]Cl>O1CCCC1>[CH3:19][O:20][CH2:21][O:1][C:2]1[C:3]2[CH:16]=[CH:15][N:14]=[CH:13][C:4]=2[S:5][C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 146738203-Hydroxy-2-phenyl-6-azabenzo[b]thiophene

Product 1

HCID 14277639HCID 14277639, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.1 g (4.8 mmol) 3-hydroxy-2-phenyl-6-azabenzo[b]thiophene and 0.116 g (4.8 mmol) of sodium hydride in 15 mL of tetrahydrofuran was stirred at room temperature for 15 minutes. Then 0.37 mL (5.0 mmol) of chloromethyl methyl ether was added and the solution was stirred at room temperature for 2 hours. The solution was partitioned between ether and water and the ether extract was concentrated to afford 1.2 g (92%) of white crystalline material, m.p. 55°-56° C.

Workup

  1. customThe solution was partitioned between ether and water
  2. extractionthe ether extract
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-8a85e2d933f0412395b293ad90acf2f4
Source dataset
uspto-grants-1990_02
Patent number
US04904672

Reaction notes

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