Chlorotrimethylsilane → Trimethylsilyl-3-benzofurancarboxylic acid

HRID 1604237Notes

Reaction equation

HRID 1604237 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]([C:22]([OH:24])=[O:23])=[CH:14]1.[CH3:25][Si:26](Cl)([CH3:28])[CH3:27]>C1COCC1.CCCCCC>[CH3:25][Si:26]([C:14]1[O:13][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]=1[C:22]([OH:24])=[O:23])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 5956551-Benzofuran-3-carboxylic acidHCID 178418339Butyllithium

Product 1

HCID 10857390Trimethylsilyl-3-benzofurancarboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diisopropylamine (4 mL) in 20 mL THF at -60° C. was added 2.5 M of n-BuLi in hexane (17 mL), and the solution was stirred at between -20 and -60° C. for 1 h. To this, a solution of 3-benzofurancarboxylic acid (2.6 g) in 30 mL THF was added at <-70° C. After 1 h, TMSCl (7 mL) was added at <-70° C., and stirring was continued for an additional 1 h. The solution was allowed to warm to 0° C., quenched with 2 N HCl and extracted with methylene chloride. The organic solution was washed with brine, dried and concentrated to give 3.6 g of 2-(trimethylsilyl-3-benzofurancarboxylic acid.

Workup

  1. waitAfter 1 h
  2. stirringstirring
  3. waitwas continued for an additional 1 h
  4. customquenched with 2 N HCl
  5. extractionextracted with methylene chloride
  6. washThe organic solution was washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-44b426a7c7294f05915ee07ba34cfc90
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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