HCID 90456112, compound → HCID 90461035, compound

HRID 2202123Notes

Reaction equation

HRID 2202123 reaction equation
[OH:1][CH2:2][C:3]1[N:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[N:5][C:4]=1[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>ClCCl.O=[Mn]=O>[CH:2]([C:3]1[N:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[N:5][C:4]=1[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1)=[O:1]

Participants

4

Reactant 1

HCID 90456112HCID 90456112, compound

Product 1

HCID 90461035HCID 90461035, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(5-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)benzonitrile (100 mg, 0.30 mmol, 1.00 equiv) and MnO2 (260 mg, 2.99 mmol, 10.00 equiv) in dichloromethane (10 mL) was stirred at room temperature for 1 h. The solid material was removed by filtration. The filtrate was concentrated under vacuum to yield 64 mg (64%) of 4-(5-formyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)benzonitrile as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ 9.94 (s, 1H), 7.93 (s, 1H), 7.76-7.56 (m, 4H), 5.75 (s, 2H), 3.66 (t, J=9.4 Hz, 2H), 0.94 (t, J=9.4 Hz, 2H), 0.04 (s, 9H) ppm. LCMS (method A, ESI): RT=1.57 min, m/z=328.0 [M+H]+.

Workup

  1. customThe solid material was removed by filtration
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-4196f21987af40e1aefc5d46a6276916
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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