HCID 57971674, compound → HCID 57971713, compound

HRID 2360621Notes

Reaction equation

HRID 2360621 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-ae7ae4e963304a0fab34b86c9936294d
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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