Ammonium Chloride → HCID 58609721, compound

HRID 1371274Notes

Reaction equation

HRID 1371274 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]Br)[CH:26]([CH3:28])[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][C:26]1([CH3:28])[CH3:27])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 59464758Ethyl 2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]acetateHCID 178418816HCID 178418816, compound

Product 1

HCID 58609721HCID 58609721, 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. 10 g (29 mmole) of ethyl 2-{[t-butyl(diphenyl)silyl]oxy}acetate was dissolved in 100 ml of tetrahydrofuran (THF) and 6.0 ml of titaniumtetraisopropoxide was added thereto. To the mixture was slowly added 37 ml of isobutylmagnesiumbromide (2.0M in THF) at −10° C., and the reaction solution was stirred for 12 hours at room temperature. 50 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 500 ml of n-hexane. The n-hexane extract was distilled under reduced pressure and purified by silica gel column to give 5.0 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 500 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-212920c2e9214bdda34aa01f6f496eda
Source dataset
uspto-grants-2007_01
Patent number
US07157448B2

Reaction notes

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