Tetrahydrofuran → HCID 12901226, compound

HRID 442536Notes

Reaction equation

HRID 442536 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([C:12]([OH:14])=O)[CH:11]=1)[NH:8][C:7](=[O:15])[CH2:6]2.O1CCCC1.[C:21]1([Li])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([C:12](=[O:14])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:11]=1)[NH:8][C:7](=[O:15])[CH2:6]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 20378346HCID 20378346, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 12901226HCID 12901226, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 1.0 g. (4.9 mole) of 5-methoxy-7-carboxyindolin-2-one in 20 ml. of tetrahydrofuran was treated dropwise with 12 ml. of commercially prepared phenyllithium solution (2.3 molar ether: benzene; 0.28 moles). After stirring for two hours the reaction mixture was poured into water and extracted several times with ethyl ether and benzene. The combined extracts were washed with water, dried over sodium sulfate and concentrated using a rotary evaporator to a solid residue which on recrystallization from acetone-water gave 259 mg. (21%) of a yellow powder which melted at 154° C.

Workup

  1. additionA suspension of 1.0 g
  2. extractionextracted several times with ethyl ether and benzene
  3. washThe combined extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customa rotary evaporator to a solid residue which
  7. customon recrystallization from acetone-water
  8. customgave 259 mg

Sources & evidence

ORD record
ord-504fbac938154116965cb6c26b274a73
Source dataset
uspto-grants-1977_08
Patent number
US04045576

Reaction notes

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