3-Methoxymethoxy-2-phenyl-7-azabenzothiophene → HCID 14277636, compound

HRID 35534Notes

Reaction equation

HRID 35534 reaction equation
COC[O:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[N:13][C:8]=2[S:7][C:6]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:20]([Li])([CH3:23])([CH3:22])[CH3:21]>O1CCCC1.CCCCCC>[CH3:21][C:20]([C:12]1[CH:11]=[CH:10][C:9]2[C:5]([OH:4])=[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:7][C:8]=2[N:13]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 146738183-Methoxymethoxy-2-phenyl-7-azabenzothiopheneHCID 178418306HCID 178418306, compound

Product 1

HCID 14277636HCID 14277636, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 2.72 g (10.0 mmol) of 3-methoxymethoxy-2-phenyl-7-azabenzothiophene in 20 mL of dry tetrahydrofuran was cooled to -78° C. To this was added 11 mL of a 1.0M solution of t-butyllithium in hexane and the solution was allowed to warm to room temperature. The solution was quenched with methanol and stirred in air for 60 minutes, then partitioned between ether and water. The aqueous layer was washed with two portions of ether and the combined extracts were washed with brine, dried, and concentrated to an oil. The oil was dissolved in 10 mL methanol and 10 mL of 2M HCl and stirred at room temperature for 24 hours. The solution was partitioned between ether and water and the ether layer dried and concentrated. Recrystallization from ether-hexane afforded 2.43 g (84%) of pale yellow needles, m.p. 181°-183° C.

Workup

  1. customThe solution was quenched with methanol
  2. custompartitioned between ether and water
  3. washThe aqueous layer was washed with two portions of ether
  4. washthe combined extracts were washed with brine
  5. customdried
  6. concentrationconcentrated to an oil
  7. dissolutionThe oil was dissolved in 10 mL methanol
  8. stirring10 mL of 2M HCl and stirred at room temperature for 24 hours
  9. customThe solution was partitioned between ether and water
  10. dry with materialthe ether layer dried
  11. concentrationconcentrated
  12. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-6e71c9af04b14b70a58865887b392b4a
Source dataset
uspto-grants-1988_08
Patent number
US04767766

Reaction notes

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