1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carbaldehyde → (1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)methanol

HRID 326774Notes

Reaction equation

HRID 326774 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH:12]=[O:13].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 136002351-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 21877600(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)methanolYield 89.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole-2-carboxaldehyde (prepared according to procedures described by J. P. Whitten et al., J. Org. Chem., 51 (1986), 1891) (9.95 g, 44.0 mmol) in dry ether (40 ml) was dropped into a suspension of lithium aluminum hydride (0.42 g, 12.0 mmol) in dry ether (40 ml) and stirring was continued for 4 hours at room temperature. Then ice-water was added carefully, and the precipitated aluminum hydroxide was filtered off and washed with ether. The aqueous phase was separated and the organic phase was washed with water, dried over sodium sulfate an evaporated in vacuo to leave an oil (9.0 g) which crystallized spontaneously. Yield: 7.1 g, m.p. 68°-69° C. (from pentane).

Workup

  1. filtrationthe precipitated aluminum hydroxide was filtered off
  2. washwashed with ether
  3. customThe aqueous phase was separated
  4. washthe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customan evaporated in vacuo

Sources & evidence

ORD record
ord-550deb02136e4a33927e2fb8b40d58a3
Source dataset
uspto-grants-1993_12
Patent number
US05270334

Reaction notes

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