Dimethylformamide → 4-t-Butyldiphenylsiloxy-2,6-dimethoxybenzaldehyde

HRID 460371Notes

Reaction equation

HRID 460371 reaction equation
C([Li])CCC.CCCCCC.[O:12]([C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[CH:31]=1)[Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C)[CH:42]=[O:43].[Cl-].[NH4+]>C(OCC)C>[O:12]([C:30]1[CH:35]=[C:34]([O:36][CH3:37])[C:33]([CH:42]=[O:43])=[C:32]([O:38][CH3:39])[CH:31]=1)[Si:13]([C:26]([CH3:28])([CH3:29])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 693655901-t-Butyldiphenylsiloxy-3,5-dimethoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 877994184-t-Butyldiphenylsiloxy-2,6-dimethoxybenzaldehydeYield 41.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under nitrogen, a 1.60 M solution of n-butyl lithium in hexane (31 mL, 49 mmol) was added to a solution of 1-t-butyldiphenylsiloxy-3,5-dimethoxybenzene (14.68 g, 39.0 mmol) in anhydrous diethyl ether (200 mL) stirred in an ice bath. The reaction mixture was stirred at 35° C. for 3 hours and cooled in the ice bath, followed by the addition of dimethylformamide (9.21 mL, 119.4 mmol). After stirring at room temperature for 1 hour, saturated aqueous ammonium chloride was added, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 4-t-butyldiphenylsiloxy-2,6-dimethoxybenzaldehyde as a colorless crystalline powder (melting point: 177.5–120.0° C.) (6.77 g, yield: 41%).

Workup

  1. stirringThe reaction mixture was stirred at 35° C. for 3 hours
  2. stirringAfter stirring at room temperature for 1 hour
  3. extractionthe mixture was extracted with diethyl ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-35628d30a8cc447b9fbdd15e5ffa343c
Source dataset
uspto-grants-2007_03
Patent number
US07196101B2

Reaction notes

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