Triethylsilane → HCID 69557038, compound

HRID 479137Notes

Reaction equation

HRID 479137 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH:5]([O:34][CH3:35])[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]3[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=3)[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:36])[CH:5]([O:34][CH3:35])[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]3[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:10][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 69556682HCID 69556682, compound

Product 1

HCID 69557038HCID 69557038, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.173 g of the above prepared 3-(4-{2-[2-(3,5-dichloro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-yl)-3-hydroxy-2-methoxy-propionic acid ethyl ester (0.31 mmol) was dissolved in 1.0 ml of trifluoroacetic acid, treated at 0° with 0.250 ml of triethylsilane (5 eq.) and then kept for 4 h at this temperature, when TLC indicated the disappearance of starting material. The reaction mixture was then poured onto crashed ice/AcOEt/NaHCO3 (pH of aq. layer ˜7.5), the organic layer washed with water and brine (pH of aq. phase˜8), dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=85/15) afforded 0.143 g of the title compound as white crystals of mp. 100-102°.

Workup

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

Sources & evidence

ORD record
ord-01f7c167eabb45c89b4eabf8f8299eea
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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