Imidazole → HCID 21110474, compound

HRID 1766940Notes

Reaction equation

HRID 1766940 reaction equation
O1C=C(CO)C(CO)=C1.N1C=CN=C1.C([Si](Cl)(C)C)(C)(C)C.[Si:23]([O:30][CH2:31][C:32]1[C:36]([CH2:37][O:38][Si](C(C)(C)C)(C)C)=[CH:35][O:34][CH:33]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>O1CCCC1>[Si:23]([O:30][CH2:31][C:32]1[C:36]([CH2:37][OH:38])=[CH:35][O:34][CH:33]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 84477Furan-3,4-diyldimethanol2×HCID 21110455HCID 21110455, compound

Product 1

HCID 21110474HCID 21110474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to a similar procedure to that described in Example 21-(2), 3,4-furandimethanol (described in J. Org. Chem., 65, 6153 (2000); 3.4 g, 26.5 mmol) was reacted with imidazole (1.80 g, 26.4 mmol) and tert-butylchlorodimethylsilane (4.00 g, 26.5 mmol) in tetrahydrofuran (50 ml), and the reaction mixture was worked up to afford a mixture of the title compound, 3,4-furandimethanol and 3,4-bis[(tert-butyldimethylsilyl)oxymethyl]furan. The mixture was subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:hexane=3:17˜4:16) to afford the title compound (3.20 g, 50% yield) as a colorless oil.

Workup

  1. customto afford

Sources & evidence

ORD record
ord-92d40dcfcfc94649a5f48ee40d2e73bf
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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