Di-tert-butyl oxalate → HCID 67487680, compound

HRID 1865412Notes

Reaction equation

HRID 1865412 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:22](OC(C)(C)C)(=[O:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH2:10][C:22](=[O:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 69651Di-tert-butyl oxalate2×HCID 2733832Lithium HexamethyldisilazideHCID 27580583',5'-Dichloroacetophenone

Product 1

HCID 67487680HCID 67487680, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the product from step B (4.1 g, 21.7 mmol) in 100 mL of diethyl ether at −78° C. was added lithium bis(trimethylsilyl)amide (23.9 mL, 23.9 mmol). After 50 min at −78° C. di-tert-butyl oxalate (4.18 g, 20.66 mmol) was added as a solid. The cold bath was removed and after 2 h an additional portion of di-tert-butyl oxalate (530 mg, 2.6 mmol) was added and stirring continued at ambient temperature for 16 h. The reaction was quenched by adding 150 mL of 1N hydrochloric acid and stirring for 1 h. The mixture was extracted with ethyl acetate and the organic layer washed with brine, dried over magnesium sulfate, and concentrated in vacuo to provide the title compound as an oil which was used without further purification. 1H NMR (500 MHz, CDCl3) δ: 7.84 (d, J=1.9 Hz, 2H); 7.59 (d, J=1.9 Hz, 1H); 6.93 (s, 1H); 1.56 (s 9H).

Workup

  1. additionwas added
  2. customThe reaction was quenched
  3. additionby adding 150 mL of 1N hydrochloric acid
  4. stirringstirring for 1 h
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic layer washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7e45950d65042359dfc51913b71eb5b
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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