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

HRID 974718Notes

Reaction equation

HRID 974718 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-hydroxy-4-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,3H).

Sources & evidence

ORD record
ord-4fe5cec1ffbb4080aac35e651ae8ac19
Source dataset
uspto-grants-1997_03
Patent number
US05607625

Reaction notes

Loading…