HCID 57971674, compound → HCID 57971713, compound

HRID 548225Notes

Reaction equation

HRID 548225 reaction equation
[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10]([C:12]1[S:16][C:15]2[CH:17]=[C:18]([CH2:21][OH:22])[CH:19]=[CH:20][C:14]=2[CH:13]=1)=[O:11])[CH3:7])[CH:2]([CH3:4])[CH3:3]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10]([C:12]1[S:16][C:15]2[CH:17]=[C:18]([CH:21]=[O:22])[CH:19]=[CH:20][C:14]=2[CH:13]=1)=[O:11])[CH3:7])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 57971674HCID 57971674, compound

Product 1

HCID 57971713HCID 57971713, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid (1-isobutoxy-ethoxy) amide (600 mg, 1.86 mmol) in DCM (3 mL) was added MnO2 (2.1 g, 24.1 mmol). The mixture was stirred at ambient temperature for 30 min and then filtered through celite. The filtrate was concentrated to afford the title compound (435 mg, 82%). LCMS m/z 320 [M+−H]+, 1H NMR (300 MHz, MeOD), δ: 0.94 (6H, d J=6.7 Hz, 2×CH3), 1.45 (3H, d J=5.3 Hz, CH3), 1.87 (1H, m, CH), 3.40 (2H, m, CH2), 5.08 (1H, dd J=5.2, 10.6 Hz, CH), 7.89-8.09 (3H, m, ArH), 8.55 (1H, s, ArH), 10.11 (1H, s, CHO).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-92ea400ca063430e8e898a697fa18ee6
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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