Methanol → HCID 68485369, compound

HRID 1874946Notes

Reaction equation

HRID 1874946 reaction equation
CO.[S:3]1[C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5][CH2:4]1)[NH:12][C:11]([C:16]([O:18]CC)=[O:17])=[CH:10]3.[Li+].[OH-]>C1COCC1>[S:3]1[C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5][CH2:4]1)[NH:12][C:11]([C:16]([OH:18])=[O:17])=[CH:10]3

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68486489HCID 68486489, compound

Product 1

HCID 68485369HCID 68485369, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A methanol solution of ethyl 2,3-dihydro-7H-[1,4]oxathiino[3,2-e]indole-8-carboxylate (0.067 g, 0.25 mmol) was treated with 1 N LiOH (4 mL). The reaction mixture turned cloudy and THF was added until the cloudiness disappeared. The reaction was heated to 70° C. until TLC showed consumption of the starting material. The reaction mixture was partitioned between EtOAc and water and the basic layer was separated. The basic layer was acidified with conc. HCl and extracted with EtOAc, the layers were separated and the EtOAc was evaporated to afford the title compound (0.047 g, 80%) as a white solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 10.85 (br. s., 1H), 7.19 (d, 1H), 7.01 (s, 1H), 6.82 (d, 1H), 4.37-4.46 (m, 2H), 3.20-3.30 (m, 2H). LCMS: m/z=235.9 (M+1).

Workup

  1. customconsumption of the starting material
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. customthe basic layer was separated
  4. extractionextracted with EtOAc
  5. customthe layers were separated
  6. customthe EtOAc was evaporated

Sources & evidence

ORD record
ord-dfb02f884fa041e6a37cb5b5931b33e7
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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