Imidazole → HCID 58025809, compound

HRID 1046924Notes

Reaction equation

HRID 1046924 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:6]([O:7][CH3:8])[C:4]=1[OH:5].[CH3:12][CH:13]([Si:15](Cl)([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[CH3:14].N1C=CN=C1>CCOC(C)=O>[CH3:8][O:7][C:6]1[C:4]([O:5][Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:14])[CH3:12])=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8991o-VanillinHCID 139400Triisopropylsilyl chloride

Product 1

HCID 58025809HCID 58025809, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

O-vanillin (26.3 mmol) is mixed with TIPSCl (39.6 mmol) and imidazole (78.7 mmol) in a microwave vessel. The mixture is heated in the microwave at 100° C. for 3 minutes. The oily mixture is diluted with EtOAc (100 mL) and washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL). After drying with MgSO4, the filtrate is concentrated. The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane) to yield 3-methoxy-2-triisopropylsilanyloxy-benzaldehyde as an oil: 1H NMR (400 MHz, CDCl3) δ 10.6 (s, 1H), 7.38 (dd, J1=1.6 Hz, J2=8 Hz, 1H), 7.04 (dd, J1=1.6 Hz, J2=8 Hz, 1H), 6.93 (td, J1=8 Hz, J2=0.8 Hz, 1H), 3.82 (s, 3H), 1.34-1.25 (m, 3H), 1.1 (s, 18H); LC/MS (ES+): 309 (M+1)+.

Workup

  1. washwashed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL)
  2. dry with materialAfter drying with MgSO4
  3. concentrationthe filtrate is concentrated
  4. customThe resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane)

Sources & evidence

ORD record
ord-d20122b2062a4ece82390b082e8c5c3a
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

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