Diisopropylamine → HCID 21245405, compound

HRID 620898Notes

Reaction equation

HRID 620898 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:18][CH3:19])(=[O:17])[CH:14]([CH3:16])[CH3:15].[CH2:20]([O:22][Si:23](Cl)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[CH3:21]>O1CCCC1>[CH3:19][O:18][C:13]([O:17][Si:23]([O:27][CH2:28][CH3:29])([O:24][CH2:25][CH3:26])[O:22][CH2:20][CH3:21])=[C:14]([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 11039Methyl isobutyrateHCID 78398TriethoxychlorosilaneHCID 178418339Butyllithium

Product 1

HCID 21245405HCID 21245405, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3-necked 2-liter flask, equipped with a mechanical stirrer, thermocouple, dry-ice condenser, and a dropping funnel, was charged with tetrahydrofuran (200 mL) and diisopropylamine (70 mL, 0.50 mol) under an argon atmosphere. The mixture was cooled to 0° and n-butyllithium (313 mL, 1.6M in hexane) was added dropwise while the temperature was maintained at about 0°. The mixture was stirred for 30 minutes, followed by dropwise addition of methyl isobutyrate (57.3 mL, 0.50 mol). Stirring was continued at 0° for an additional 30 minutes and triethoxysilyl chloride (147 mL, 0.75 mol) was added. The mixture was stirred and allowed to warm up to room temperature overnight and filtered under argon to remove the precipitated lithium salts. The solvents were evaporated and the liquid residue was distilled, first using a Vigreux column, followed by spinning band distillation. The total MPTES obtained was 113.3 g (86% yield). This was identified by 1H NMR spectroscpy, IR (infrared) and GC/MS; (gas chromatography/mass spectroscopy) b.p. 59°-60°/0.15 mm Hg.

Workup

  1. customA 3-necked 2-liter flask, equipped with a mechanical stirrer
  2. temperatureThe mixture was cooled to 0°
  3. temperaturewas maintained at about 0°
  4. stirringStirring
  5. waitwas continued at 0° for an additional 30 minutes
  6. stirringThe mixture was stirred
  7. filtrationfiltered under argon
  8. customto remove the precipitated lithium salts
  9. customThe solvents were evaporated
  10. distillationthe liquid residue was distilled
  11. distillationband distillation
  12. customThe total MPTES obtained

Sources & evidence

ORD record
ord-ca09d67606da4925a9168952784ce3db
Source dataset
uspto-grants-1989_04
Patent number
US04822859

Reaction notes

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