Triethylsilane → HCID 69487387, compound

HRID 2215198Notes

Reaction equation

HRID 2215198 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH:5]([O:30][CH:31]([CH3:33])[CH3:32])[CH:6]([C:8]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[C:11]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]([CH3:29])([CH3:28])[CH3:27])[O:23][C:24]=2[CH3:25])=[CH:10][CH:9]=1)O)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:34])[CH:5]([O:30][CH:31]([CH3:33])[CH3:32])[CH2:6][C:8]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[C:11]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]([CH3:27])([CH3:28])[CH3:29])[O:23][C:24]=2[CH3:25])=[CH:10][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69489883HCID 69489883, compound

Product 1

HCID 69487387HCID 69487387, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.434 g of the above prepared 3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-3-hydroxy-2-isopropoxy-propionic acid ethyl ester (0.886 mmol) was dissolved in 4.5 ml of trifluoroacetic acid, treated at 0° with 1.408 ml of triethylsilane (10 eq.) and then kept for 2 h at 0° under vigorous stirring, when TLC indicated the disappearance of starting material. The reaction mixture was then poured onto crashed ice/AcOEt/NaHCO3, the organic layer washed with water (pH of aq. phase˜8), dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) yielded 0.322 g of the title compound as colorless oil.

Workup

  1. additionThe reaction mixture was then poured
  2. washthe organic layer washed with water (pH of aq. phase˜8)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a65d1672015a4f199c44dd39043f76e6
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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