Chlorotrimethylsilane → HCID 54410387, compound

HRID 1493433Notes

Reaction equation

HRID 1493433 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:14])[CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].Cl[Si:16]([CH3:19])([CH3:18])[CH3:17].CCCCCC>O1CCCC1>[CH2:3]([O:5][C:6]([O:14][Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:13])[CH3:4]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 11857Diethyl methylmalonate2×HCID 24758Sodium hydride

Product 1

HCID 54410387HCID 54410387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a dispersion of 3.1 g of NaH in 20 mL of tetrahydrofuran (THF) at room temperature was added 20 mL of diethylmethylmalonate, at an addition rate of 0.5 mL/minute. The mixture was kept below 30° by the use of a water/ice bath. After complete addition of the diethylmethylmalonate, the mixture was stirred for 30 minutes, then cooled to 0° and 13.5 mL of chlorotrimethylsilane was added. After 40 minutes, 10 mL of hexane was added and the mixture was stirred overnight, filtered under argon, and distilled A forerun (40°-58°, 0.32 mm) was discarded, the product distilling at 62°-64°, 0.40 mm. NMR. (CD3CN, TMS) indicates that the product is a 75/25 mixture of E/Z isomers of ECPS; major isomer: 0.303 (s, 9H, SiMe3); 1.255 (t, J=b 7 Hz, 6H, OCH2CH3); 1.754 (s, 3H, vinyl CH3); 3.988-4.250 (m, all OCH2 for both isomers. Minor isomer: 0.308 (s, 9H, SiMe3); 1.264 (t, J=7H, 6H, OCH2CH3); 1.727 (s, 3H, vinyl CH3 1.754); 3.988-4.250 (m, all OCH2 for both isomers). Anal. calc. for C11H22SiO4 : C 53.67; H 8.94. Found C 53.33; H 8.76.

Workup

  1. customThe mixture was kept below 30° by the use of a water/ice bath
  2. temperaturecooled to 0°
  3. waitAfter 40 minutes
  4. stirringthe mixture was stirred overnight
  5. filtrationfiltered under argon
  6. distillationdistilled A forerun (40°-58°, 0.32 mm)
  7. distillationthe product distilling at 62°-64°
  8. additiona 75/25 mixture of E/Z isomers of ECPS

Sources & evidence

ORD record
ord-cbc029a9460640f79a1a4b9835a5bfc1
Source dataset
uspto-grants-1991_06
Patent number
US05021524

Reaction notes

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