Oxygen → 3-HYDROXY-5-PHENYLPYRROLE
Reaction equation
C([N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:6]([O:15]C(=O)C)=[CH:5]1)(=O)C.O=O.[OH-].[Na+]>CO>[OH:15][C:6]1[CH:7]=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:4][CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
A finely divided portion of N-acetyl-3-acetoxy-5-phenylpyrrole (2) (36.8 g; 0.15 mol) was freed of oxygen by stirring in a flowing argon stream for 10 minutes, then suspended in deoxygenated MeOH (379 mL), cooled to -6° C. (in a -15° C. methanol (MeOH)/dry-ice bath) under an inert gas atmosphere and rapidly treated with an ice cold deoxygenated solution of 2N NaOH (300 mL). The reaction temperature rose immediately upon addition of base to 18° C., and after ~3 minutes the reaction mixture became homogeneous. As the reaction mixture cooled, compound (3) separated as fine crystals. After 15 minutes a solution of cold deoxygenated 2M citric acid (150 ml) was added, the resulting mixture was stirred for 10 minutes, and then filtered. The solid was washed thoroughly with deoxygenated water (200 mL), taking care to minimize exposure of the product to air, then dried under vacuum overnight to yield the title compound (22.3 g; 93.6%) as light pink tiny needles.
Workup
- additionThe reaction temperature rose immediately upon addition of base to 18° C.
- waitafter ~3 minutes the reaction mixture became homogeneous
- temperatureAs the reaction mixture cooled
- customcompound (3) separated as fine crystals
- customAfter 15 minutes a solution of cold deoxygenated 2M citric acid (150 ml)
- additionwas added
- stirringthe resulting mixture was stirred for 10 minutes
- filtrationfiltered
- washThe solid was washed thoroughly with deoxygenated water (200 mL)
- customdried under vacuum overnight
Sources & evidence
- ORD record
- ord-d49ae8930e3a4fe8bb18170378be0d0c
- Source dataset
- uspto-grants-1987_01
- Patent number
- US04637979
Reaction notes
Loading…