Sulfuric Acid → HCID 12902861, compound

HRID 262242Notes

Reaction equation

HRID 262242 reaction equation
[N+:1]([C:4]1[O:5][C:6]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26](O)=[O:27])=[CH:21][CH:20]=3)=[CH:15][C:7]=2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-:3])=[O:2].B.O.O1CCCC1.S(=O)(=O)(O)O>O1CCCC1>[OH:27][CH2:26][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:17]=[CH:18][C:6]3[O:5][C:4]([N+:1]([O-:3])=[O:2])=[C:8]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:7]=3[CH:15]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6331BoraneHCID 12902857HCID 12902857, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 12902861HCID 12902861, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 2 g. (0.00536 mole) of 4-(2-nitro-3-phenylbenzofuran-5-yl)phenylacetic acid (the product of step D of Example 1 hereof) in 100 ml. of tetrahydrofuran is cooled to 0° C. and 20 ml. of a borane solution in tetrahydrofuran is added while under a nitrogen atmosphere over 10 minutes. After warming to 20° C. the mixture is stirred for 16 hours. The solution is cooled to 0° C., 50 ml. of 1:1 water-tetrahydrofuran mixture and 15 ml. of 3N sulfuric acid are each added slowly and the mixture is stirred at 20° C. for 45 minutes. Evaporation provides a residue which crystallizes when triturated with hexane. Chromatography through silica gel in chloroform, eluting with chloroform, provides 5-[4-(2-hydroxyethyl)phenyl]-2-nitro-3-phenylbenzofuran, m.p. 86°-87° C.

Workup

  1. temperatureThe solution is cooled to 0° C.
  2. additioneach added slowly
  3. stirringthe mixture is stirred at 20° C. for 45 minutes
  4. customEvaporation
  5. customprovides a residue which
  6. customcrystallizes when
  7. customtriturated with hexane
  8. washChromatography through silica gel in chloroform, eluting with chloroform

Sources & evidence

ORD record
ord-4bd452ea23a6419597f99e645fa7cfea
Source dataset
uspto-grants-1979_05
Patent number
US04153721

Reaction notes

Loading…