Trimethylsilyldiazomethane → HCID 68528114, compound

HRID 2386194Notes

Reaction equation

HRID 2386194 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:6]=[CH:7][CH:8]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:19]>CO.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:19])=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 59451682HCID 59451682, compound

Product 1

HCID 68528114HCID 68528114, compound

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Conditions

Temperature
0 °C

Procedure

An anhydrous solution of methanol:toluene (2:5) (10.5 mL) was used to solubilize 7-(3-methoxyphenyl)heptanoic acid (0.159 g, 0.673 mmol) under an atmosphere of argon and the solution was then cooled to 0° C. Stirring was initiated and a 2 M solution of TMSCHN2 (in hexanes) (0.740 mL, 1.48 mmol) was added dropwise to the reaction solution. The yellow solution was allowed to stir for 30 minutes at room temperature before again being cooled to 0° C. The reaction was quenched with the dropwise addition of acetic acid until the characteristic yellow color of diazomethane dissipated. The solvent was removed under vacuum and the resultant suspension taken in ethyl acetate. The organic phase was washed with saturated sodium bicarbonate then brine and dried over sodium sulfate. The solvent was removed under vacuum and the target product was purified as a light yellow oil (92%, 0.139 g) using flash column chromatography (silica) with a 10% ethyl acetate:hexanes mobile phase: 1H NMR (500 MHz, CDCl3) δ 7.19 (t, 1H), 6.74 (q, 3H), 3.80 (s, 3H), 3.67 (s, 3H), 2.59 (t, 2H), 2.31 (t, 2H), 1.63 (m, 4H), 1.36 (m, 4H); 13C NMR (500 MHz, CDCl3) δ 174.17, 159.60, 144.31, 129.17, 120.82, 114.17, 110.86, 55.06, 51.41, 35.93, 34.05, 31.17, 29.01, 28.91, 24.89.

Workup

  1. stirringto stir for 30 minutes at room temperature
  2. temperaturebefore again being cooled to 0° C
  3. customThe reaction was quenched with the dropwise addition of acetic acid until the characteristic yellow color of diazomethane
  4. customThe solvent was removed under vacuum
  5. washThe organic phase was washed with saturated sodium bicarbonate
  6. dry with materialbrine and dried over sodium sulfate
  7. customThe solvent was removed under vacuum
  8. customthe target product was purified as a light yellow oil (92%, 0.139 g)

Sources & evidence

ORD record
ord-e6ee300e511646388f45fce312af25ff
Source dataset
uspto-grants-2012_09
Patent number
US08268817B2

Reaction notes

Loading…