Lithium iodide → HCID 57443971, compound

HRID 545484Notes

Reaction equation

HRID 545484 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, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester 6-methyl ester (14.90 g, 56.38-mmol) and LiI (37.96 g, 283.6 mmol) in 120 mL of anhydrous pyridine was refluxed for 3 h. After cooling to rt, the mixture was poured into ice-cold 2N HCl (800 mL). The solid formed was filtered and washed with 3×100 mL of water. After drying, the solid was crystallized from MeOH to give benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester as a pale solid. 1H NMR (DMSO-d6, 200 MHz) δ 8.66 (s, 1H), 8.21 (s, 1H), 8.08 (d, J=8.4 Hz, 1H), 7.96 (dd, J=8.4, 1.0 Hz, 1H), 4.34 (q, J=7.2 Hz, 2H), 1.40 (t, J=6.8 Hz, 3H). MS (EI): cal'd 251.0 (MH+), exp 251.1 (MH+).

Workup

  1. temperaturewas refluxed for 3 h
  2. customThe solid formed
  3. filtrationwas filtered
  4. washwashed with 3×100 mL of water
  5. customAfter drying
  6. customthe solid was crystallized from MeOH

Sources & evidence

ORD record
ord-a260dca6ec3b4f87bf79b9e98a250620
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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