Lithium iodide → HCID 57443971, compound

HRID 1011645Notes

Reaction equation

HRID 1011645 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].[Li+].[I-]>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 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of benzo[b]-thiophene-2,6-dicarboxylic acid 2-ethyl ester 6-methyl ester (16.19 g, 61.26 mmol) and LiI (34.68 g, 259.11 mmol) in 500 ml anhydrous pyridine was refluxed for 3 days. After cooling to rt, the mixture was poured into ice-cold 2N HCl (1000 mL). The solid was collected, washed with water and dried. The solid was crystallized from methanol to give benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester as a pale solid (11.65 g, 76%). MS: calc'd 251 (MH+), exp 251 (MH+). 1H NMR (d6-DMSO, 400 MHz), 8.69 (s, 1H), 8.26 (s, 1H), 8.11 (d, 1H, J=8.4 Hz), 7.98 (d, 1H, J=8.4 Hz), 4.37 (q, 2H, J=6.8 Hz), 1.35 (t, 3H, J=7.2 Hz).

Workup

  1. temperaturewas refluxed for 3 days
  2. customThe solid was collected
  3. washwashed with water
  4. customdried
  5. customThe solid was crystallized from methanol

Sources & evidence

ORD record
ord-8c48a1c9b42d4528ba9795b8c4544603
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

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