Chlorotrimethylsilane → HCID 10856456, compound

HRID 1645325Notes

Reaction equation

HRID 1645325 reaction equation
[C:1]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[CH:7].[Li]CCCC.[CH3:15][Si:16](Cl)([CH3:18])[CH3:17]>C1COCC1>[CH3:15][Si:16]([CH3:18])([CH3:17])[C:7]#[C:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 43779506-Heptynoic acidHCID 178418339Butyllithium

Product 1

HCID 10856456HCID 10856456, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of hept-6-ynoic acid (1.90 g, 14.8 mmol) in anhydrous THF (90 mL) at −78° C. was treated with n-BuLi (2.3 M in hexanes, 14.5 mL, 33.3 mmol). After stirring for 2 min, TMSCl (5.8 mL, 46.0 mmol) was added. The reaction mixture was allowed to warm slowly to 25° C. and was stirred for 1 h. The reaction was quenched with the addition of aqueous 2 N HCl and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. Column chromatography (SiO2, 4×6 cm, 20% EtOAc-hexanes) afforded 7-(trimethylsilyl)hept-6-ynoic acid (2.7 g, 13.6 mmol, 92%) as a white solid: 1NMR (CDCl3, 500 MHz) δ 2.40 (t, 2H, J=7.4 Hz), 2.24 (t, 2H, J=7.3 Hz), 1.78-1.72 (m, 2H), 1.62-1.56 (m, 2H), 0.15 (s, 9H).

Workup

  1. stirringwas stirred for 1 h
  2. customThe reaction was quenched with the addition of aqueous 2 N HCl
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0edd26df302b40cf8cd5d555a2c31533
Source dataset
uspto-grants-2012_02
Patent number
US08124778B2

Reaction notes

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