Imidazole → Diethyl (4-t-butyldimethylsilyloxy-3-methoxy-5-methylbenzyl)phosphonate

HRID 48924Notes

Reaction equation

HRID 48924 reaction equation
N1C=CN=C1.[OH:6][C:7]1[C:21]([CH3:22])=[CH:20][C:10]([CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])=[CH:9][C:8]=1[O:23][CH3:24].[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[OH-].[NH4+]>CN(C=O)C.O>[Si:25]([O:6][C:7]1[C:21]([CH3:22])=[CH:20][C:10]([CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])=[CH:9][C:8]=1[O:23][CH3:24])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 14923Ammonium HydroxideHCID 28928tert-Butyldimethylsilyl chlorideHCID 57349790Diethyl [(4-hydroxy-3-methoxy-5-methylphenyl)methyl]phosphonate

Product 1

HCID 91612824Diethyl (4-t-butyldimethylsilyloxy-3-methoxy-5-methylbenzyl)phosphonateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Imidazole (7.08 g, 104 mmol) was added portionwise to a well stirred mixture of diethyl (4-hydroxy-3-methoxy-5-methylbenzyl)phosphonate (10 g, 35 mmol) and t-butyldimethylsilyl chloride (7.84 g, 52 mmol) in 25 ml DMF and stirring was continued for 16 h at room temperature. The mixture was poured into water kept at 0° C. to which was added a 25% ammonium hydroxide solution until pH 7 was reached. The aqueous phase was extracted with chloroform, the organic phase was dried over MgSO4. Evaporation of the solvent gave 14 g (100%) of diethyl (4-t-butyldimethylsilyloxy-3-methoxy-5-methylbenzyl)phosphonate as a dark oil.

Workup

  1. stirringstirring
  2. customkept at 0° C. to which
  3. extractionThe aqueous phase was extracted with chloroform
  4. dry with materialthe organic phase was dried over MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-bdcabf5f420b4fa685a42abb875f87fb
Source dataset
uspto-grants-2004_03
Patent number
US06706698B2

Reaction notes

Loading…