Methanol → 7-(Hydroxyphenylmethyl)-3-hydroxy-2-phenyl-6-azabenzo[b]thiophene

HRID 35541Notes

Reaction equation

HRID 35541 reaction equation
[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]1[C:8]2[S:9][C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11](COC)[C:7]=2[CH:6]=[CH:5][N:4]=1.C[OH:28]>Cl>[OH:1][CH:2]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:3]1[C:8]2[S:9][C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([OH:28])[C:7]=2[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 200626177-(Hydroxyphenylmethyl)-3-methoxymethyl-2-phenyl-6-azabenzo[b]thiophene

Product 1

HCID 142776407-(Hydroxyphenylmethyl)-3-hydroxy-2-phenyl-6-azabenzo[b]thiopheneYield 93%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 0.61 g (1.8 mmol) of 7-(hydroxyphenylmethyl)-3-methoxymethyl-2-phenyl-6-azabenzo[b]thiophene in 2.7 mL of 2M HCl and 2.7 mL of methanol was heated at reflux for 30 minutes. The solution was cooled and partitioned between ethyl acetate and water. The ethyl acetate layer was dried and concentrated to afford 0.50 g (93%) of white solid, m.p. 214°-215° C.

Workup

  1. temperatureat reflux for 30 minutes
  2. temperatureThe solution was cooled
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-44e7abbd23544adebbf3d4dfcf806617
Source dataset
uspto-grants-1988_08
Patent number
US04767766

Reaction notes

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