Triethylsilane → HCID 69487539, compound

HRID 2215202Notes

Reaction equation

HRID 2215202 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([O:29][CH2:30][CH3:31])[CH:6]([C:8]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[C:11]([O:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[O:22][C:23]=2[CH3:24])=[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:32])[CH:5]([O:29][CH2:30][CH3:31])[CH2:6][C:8]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[C:11]([O:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]([CH3:26])([CH3:28])[CH3:27])[O:22][C:23]=2[CH3:24])=[CH:10][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 694870563-[4-(2-tert-Butyl-5-methyl-oxazol-4-ylmethoxy)-benzo[b]thiophen-7-yl]-2-ethoxy-3-hydroxy-propionic acid ethyl ester

Product 1

HCID 69487539HCID 69487539, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.200 g of the above prepared 3-[4-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxy)-benzo[b]thiophen-7-yl]-2-ethoxy-3-hydroxy-propionic acid ethyl ester (0.433 mmol) was dissolved in 1.4 ml of trifluoroacetic acid, treated at 0° with 0.688 ml of triethylsilane (10 eq.) and then kept for 6 h at 0° under vigorous stirring. The reaction mixture was then poured onto crashed ice/AcOEt/NaHCO3, the organic layer washed with water (pH of aq. phase ˜8), dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) yielded 0.127 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 magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-fd8c1af79b9b42c08b40d2c4524a0b43
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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