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

HRID 1084741Notes

Reaction equation

HRID 1084741 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 aoetate 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 aoetate and water
  4. dry with materialThe ethyl acetate layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-50cd0fe8dd1a450293e03bc8f529ba1c
Source dataset
uspto-grants-1991_04
Patent number
US05006532

Reaction notes

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