Tetrahydrofuran → HCID 12351494, compound

HRID 1413963Notes

Reaction equation

HRID 1413963 reaction equation
[C:1]([C:6]1[CH:7]=C2[C:12](=[CH:13][CH:14]=1)[NH:11]C(=S)C2C)([O:3][CH2:4][CH3:5])=[O:2].[CH3:17][C:18](C)([O-:20])[CH3:19].[K+].[O:23]1CCCC1>>[C:1]([C:6]1[CH:7]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:19](=[O:23])[C:18]2=[O:20])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 20289278HCID 20289278, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 12351494HCID 12351494, compoundYield 60%

Procedure

According to the general procedure, 4.06 g of 5-carboethoxy-3-methylthiooxindole and an E.Q. of sublimed potassium t-butoxide in 250 ml of dry tetrahydrofuran was stirred and aerated for 6 h at 0° C. and 18 h at 25° C. Acidification with 1.35 ml of conc. hydrochloric acid in 25 ml of water, followed by extraction with ether and normal workup (vide supra), gave a yellow solid which was recrystallized from ethyl acetate to yield 2.20 g (60%) of 5-carboethoxyisatin, mp 205°-206° C. EXAMPLE 3: 5-Methylisatin

Workup

  1. extractionAcidification with 1.35 ml of conc. hydrochloric acid in 25 ml of water, followed by extraction with ether and normal workup (vide supra)
  2. customgave a yellow solid which
  3. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-338be66bcd834462a6dbc25bac627de8
Source dataset
uspto-grants-1981_02
Patent number
US04252723

Reaction notes

Loading…