Lithium iodide → HCID 57443971, compound

HRID 548221Notes

Reaction equation

HRID 548221 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:10][C:9]=2[CH:18]=1)=[O:4].[I-].[Li+]>N1C=CC=CC=1>[CH3:17][CH2:16][O:15][C:13]([C:11]1[S:10][C:9]2[CH:18]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7][C:8]=2[CH:12]=1)=[O:14]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 53233006HCID 53233006, compound

Product 1

HCID 57443971HCID 57443971, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester 6-methyl ester (3.9 g, 14.77 mmol) and Lithium iodide (10 g, 74.6 mmol) in anhydrous pyridine (30 ml, 9 vol) was stirred at reflux for 16 h. After cooling to r.t., the mixture was added (either as a melt or chipped out) to ice-cold 2N HCl (200 mL). The solid formed was isolated by filtration and washed with water (3×50 mL). The product was purified by recrystallisation from methanol to give the title compound (1.8 g, 49%). LCMS m/z 251 [M++H]+, 1H NMR (300 MHz, DMSO), δ: 1.35 (3H, t J=6.9 Hz, CH3), 4.38 (2H, q J=7.1 Hz, CH2), 7.99 (1H, d J=8.3 Hz, ArH), 8.12 (1H, d J=8.3 Hz, ArH), 8.27 (1H, s, ArH), 8.70 (1H, s, ArH).

Workup

  1. temperatureat reflux for 16 h
  2. additionthe mixture was added (either as a melt
  3. customThe solid formed
  4. customwas isolated by filtration
  5. washwashed with water (3×50 mL)
  6. customThe product was purified by recrystallisation from methanol

Sources & evidence

ORD record
ord-78960ef38ba64d25914f479716ff2caf
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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