Chloromethyl Methyl Ether → 3-Methoxymethoxy-2-phenyl-7-azabenzothiophene

HRID 1084733Notes

Reaction equation

HRID 1084733 reaction equation
[OH:1][C:2]1[C:3]2[CH:16]=[CH:15][CH:14]=[N:13][C:4]=2[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].[CH3:23][O:24][CH2:25]Cl>O1CCCC1>[CH3:23][O:24][CH2:25][O:1][C:2]1[C:3]2[CH:16]=[CH:15][CH:14]=[N:13][C:4]=2[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 10998740HCID 10998740, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 146738183-Methoxymethoxy-2-phenyl-7-azabenzothiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4.54 g (20 mmol) of 3-hydroxy-2-phenyl-7-azabenzo[b]thiophene and 2.75 g (22 mmol) of potassium t-butoxide in 50 mL of tetrahydrofuran was stirred until the solid dissolved. Then 2.0 g (25 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 aqueous layer was washed with two portions of ether. The ether extracts were washed with brine, dried over MgSO4, and concentrated to 4.33 g (80%) of an oil that crystallized upon standing, m.p. 54° C.

Workup

  1. dissolutiondissolved
  2. stirringthe solution was stirred at room temperature for 2 hours
  3. customThe solution was partitioned between ether and water
  4. washthe aqueous layer was washed with two portions of ether
  5. washThe ether extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to 4.33 g (80%) of an oil that
  8. customcrystallized

Sources & evidence

ORD record
ord-dc08f0932f574480857804b0ca43dada
Source dataset
uspto-grants-1991_04
Patent number
US05006532

Reaction notes

Loading…