Ammonium Chloride → HCID 58609719, compound

HRID 1371271Notes

Reaction equation

HRID 1371271 reaction equation
[Si:1]([O:18][CH2:19][C:20]([O:22]CC)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([Mg]Cl)[CH2:26][CH3:27].[Cl-].[NH4+]>O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[Si:1]([O:18][CH2:19][C:20]1([OH:22])[CH2:25][CH:26]1[CH3:27])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 59464758Ethyl 2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]acetateHCID 178455855HCID 178455855, compound

Product 1

HCID 58609719HCID 58609719, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

According to the description in a reference (see: Syn. Lett. 07, 1053–1054, 1999), the title compound was prepared as follows. 50 g (146 mmole) of ethyl 2-{[t-butyl(diphenyl)silyl]oxy}acetate was dissolved in 700 ml of tetrahydrofuran (THF) and 30.0 ml of titaniumtetraisopropoxide was added thereto. To the mixture was slowly added 290 ml of propylmagnesiumchloride (2.0M in THF) at −10° C., and the reaction solution was stirred for 12 hours at room temperature. 200 ml of saturated ammonium chloride was added to stop the reaction. The tetrahydrofuran (THF) used as a solvent was removed by distillation under reduced pressure, and the reaction mixture was extracted twice with 2000 ml of n-hexane. The n-hexane extract was distilled under reduced pressure and purified by silica gel column to give 42 g of the title compound.

Workup

  1. customthe title compound was prepared
  2. customat −10° C.
  3. customthe reaction
  4. customwas removed by distillation under reduced pressure
  5. extractionthe reaction mixture was extracted twice with 2000 ml of n-hexane
  6. extractionThe n-hexane extract
  7. distillationwas distilled under reduced pressure
  8. custompurified by silica gel column

Sources & evidence

ORD record
ord-67bed840c6d143ffb5e3df872efd547f
Source dataset
uspto-grants-2007_01
Patent number
US07157448B2

Reaction notes

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