Lithium Chloride → HCID 178447564, compound

HRID 920865Notes

Reaction equation

HRID 920865 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[Cl-].[Zn:22](OC(C(C)(C)C)=O)[O:23][C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25]>C1COCC1>[C:24]([O-:25])(=[O:23])[C:26]([CH3:29])([CH3:28])[CH3:27].[C:1]([O:5][C:6]([O:8][C:9]1[CH:19]=[CH:18][CH:17]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]=1[Zn+:22])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 433294Lithium Chloride2×HCID 67981607Ethyl 3-[(tert-butoxycarbonyl)oxy]benzoateHCID 178447632HCID 178447632, compound

Product 1

HCID 178447564HCID 178447564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a dry and argon-flushed Schlenk-flask, equipped with a magnetic stirring bar and a septum, ethyl 3-((tert-butoxycarbonyl)oxy)benzoate (266 mg, 1.00 mmol) was dissolved in dry THF (3.0 mL). TMPMgCl.LiCl (1.00 mL, 1.2 M in THF, 1.20 mmol) was added dropwise and the mixture was stirred for 4 h at 0° C. A solution of Zn(OPiv)2.2 LiCl (529 mg, 1.50 mmol) in 1.5 mL of dry THF was added and the mixture was slowly warmed to 22° C. The solvent was removed in vacuo and (2-((tert-butoxycarbonyl)oxy)-6-(ethoxycarbonyl)phenyl)zinc pivalate was obtained as a orange solid.

Workup

  1. customIn a dry
  2. customargon-flushed Schlenk-flask
  3. customequipped with a magnetic stirring bar
  4. temperaturethe mixture was slowly warmed to 22° C
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0ca47f3ee09a4cdd8af9db9538ac10a5
Source dataset
uspto-grants-2016_03
Patent number
US09273070B2

Reaction notes

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