Acetic Acid → HCID 68534625, compound

HRID 2108672Notes

Reaction equation

HRID 2108672 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])[CH:5]=[C:4]([CH3:19])[C:3]=1[CH:20]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([Si](C(C)C)(C(C)C)C(C)C)[CH:26]=[C:25]2[CH:41]([CH3:43])[CH3:42])O.CC(O)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOC(C)=O.O>[CH3:19][C:4]1[CH:5]=[C:6]([O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:11])[CH3:12])[CH:7]=[C:2]([CH3:1])[C:3]=1[CH2:20][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[C:25]2[CH:41]([CH3:43])[CH3:42]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 68530750HCID 68530750, compound

Product 1

HCID 68534625HCID 68534625, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2,6-dimethyl-4-triisopropylsilanyloxyphenyl)-(3-isopropyl-1-triisopropylsilyl-1H-indol-5-yl)-methanol (1.86 g, 3.0 mmol) in CH2Cl2 (20 ml) was added tiethylsilane (1.74 g, 15.0 mmol), followed by AcOH (1.11 ml), then TFA (1.11 ml, 15.0 mmol). The reaction was stirred at r.t. for 1 hr, the reaction mixture was diluted with EtOAc and water and the layers were separated. The EtOAc layer was collected and the water layer was further extracted with EtOAc once. The combined organic layers was washed with Sat. NaHCO3, water and brine, dried over MgSO4, filtrated and concentrated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:49) to afford 5-(2,6-dimethyl-4-triisopropylsilyloxybenzyl)-3-isopropyl-1H-indole (1.0 g, 74.6%): 1H NMR (200 MHz, CDCl3): δ 7.59 (s, 1H), 7.02 (d, J=8.2 Hz, 1H), 6.97 (s, 1H), 6.70 (s, 1H), 6.63 (d, J=8.2 Hz, 1H), 3.89 (s, 2H), 2.88 (m, 1H), 2.01 (s, 6H), 1.2 (m, 3H), 1.05 (d, J=6.6 Hz, 6H), 0.99 (d, J=6.2 Hz, 18H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:49); Rf=0.70.

Workup

  1. customthe layers were separated
  2. customThe EtOAc layer was collected
  3. extractionthe water layer was further extracted with EtOAc once
  4. washThe combined organic layers was washed with Sat. NaHCO3, water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with ethyl acetate-hexanes (1:49)

Sources & evidence

ORD record
ord-3d032feba26d4ed08e7ce6411ea6b74d
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

Loading…