Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | HCID 44447719 | HCID 44447719 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Propylene Glycol | HCID 1030 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 44447720 | HCID 44447720 | 76.3% |
Reaction Steps
To a solution of 2b (67.0 mg, 0.14 mmol) in THF (3 mL) and 1,2-propanediol (3 mL) was added aqueous potassium hydroxide (0.40 mL of a 8 M solution in water, 3.20 mmol). The mixture was stirred at 110° C. for 18 h and then cooled to room temperature. The reaction mixture was diluted with water, acidified with 1 N hydrochloric acid and extracted three times with EtOAc. The combined organic extracts were washed with water, dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel; dichloromethane/methanol/concentrated aqueous ammonium hydroxide (85:15:1) gave a solid (48.0 mg) that was triturated with ether/hexane to provide 2c as a solid (38 mg), m.p. 205-210° C. (dec.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07629467B2 |
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| Source dataset | uspto-grants-2009_12 |
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| ORD ID | ord-3133dbd6693f43f0a433753d452ac0a1 |
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| Source note | uspto-grants-2009_12 |
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