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

HRID 35533Notes

Reaction equation

HRID 35533 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-bef28c60cfed41eea226d051b2639270
Source dataset
uspto-grants-1988_08
Patent number
US04767766

Reaction notes

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