Imidazole → Methyl 3-tert-butyldimethylsilyloxy-4-methoxybenzoate

HRID 1956122Notes

Reaction equation

HRID 1956122 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1.CN(C)C=O>CCCCCC>[Si:14]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 11335452Methyl 3-tert-butyldimethylsilyloxy-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of methyl 3-hydroxy4-methoxybenzoate (120 mg, 0.66 mmol, prepared in Step 1, above), tert-butyldimethylsilyl chloride: (109 mg, 0.72 mmol), imidazole (98 mg, 1.24 mmol) and dimethylformamide (DMF, 2 ml) was stirred at room temperature over night. Extractive workup with hexane gave 90 mg of methyl 3-tert-butyldimethylsilyloxy-4-methoxybenzoate. NMR(δ): 0.18 (s, 3H), 1.00 (s, 9H),3.88 (s, 3H), 3.89 (s, 3 H).

Sources & evidence

ORD record
ord-72cdf176d10a4d42a43e1211ebca6809
Source dataset
uspto-grants-1998_07
Patent number
US05780249

Reaction notes

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