HCID 57443968, compound → Ethyl 6-formylbenzo[b]thiophene-2-carboxylate

HRID 500673Notes

Reaction equation

HRID 500673 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH2:15][OH:16])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH:15]=[O:16])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 57443968HCID 57443968, compound

Product 1

HCID 57443969Ethyl 6-formylbenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid ethyl ester (2.651 g, 11.22 mmol) in 110 mL of CH2Cl2 was added MnO2 (13.50 g). The mixture was allowed to stir at rt for 30 min and then filtered through a pad of Celite. The filtrate was concentrated and dried to give 6-formyl-benzo[b]thiophene-2-carboxylic acid ethyl ester as a pale solid. 1H NMR (CDCl3, 200 MHz) δ 10.09 (s, 1H), 8.34 (s, 1H), 8.07 (s, 1H), 7.97 (d, J=8.0 Hz, 2H), 7.88 (dd, J=8.4, 1.4 Hz, 1H), 4.40 (q, J=7.0 Hz, 2H), 1.41 (t, J=7.0 Hz, 3H). MS (EI): cal'd 235.0 (M+), exp 235.1 (M+).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated
  3. customdried

Sources & evidence

ORD record
ord-8919e1c728f649779838fb23d5252592
Source dataset
uspto-grants-2010_08
Patent number
US07772238B2

Reaction notes

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