Chlorotrimethylsilane → HCID 22134407, compound

HRID 654474Notes

Reaction equation

HRID 654474 reaction equation
[N:1]1([CH2:10][C:11]([OH:13])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[Si](C)(C)[CH3:16]>CCOCC>[O:13]=[C:11]([CH3:16])[CH2:10][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 904481H-Indole-1-acetic acid

Product 1

HCID 22134407HCID 22134407, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of indole-N-acetic acid (KNK, 10 g, 57 mmol) in dry ether (150 mL) was added dropwise at 0° C. a solution of MeLi (75 mL, 1.4M in ether as LiBr complex). The reaction mixture was then stirred at r.t. for 2 hrs. Chlorotrimethylsilane (70 mL, 0.57 mol) was added dropwise at 0° C. Then the cooling bath was removed and 1N HCl (70 mL) was added at r.t. The aqueous portion was extracted with ethyl acetate and the combined organic phase was washed with brine, dried over MgSO4 and evaporated. Purification by flash chromatography usine 30% ethyl acetate in hexanes gave the title compound.

Workup

  1. customThen the cooling bath was removed
  2. addition1N HCl (70 mL) was added at r.t
  3. extractionThe aqueous portion was extracted with ethyl acetate
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customPurification by flash chromatography usine 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-099e0547284d4d04b0b7c56286ee82f4
Source dataset
uspto-grants-1992_07
Patent number
US05132319

Reaction notes

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