Hydrochloric Acid → HCID 619996, compound

HRID 1885480Notes

Reaction equation

HRID 1885480 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Mg].C(O[C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])C.Cl>O1CCCC1>[O:28]=[C:22]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 82131-BromohexadecaneHCID 5462224Magnesium

Product 1

HCID 619996HCID 619996, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of 40 ml of hexadecyl bromide in 250 ml of tetrahydrofuran containing 3.64 g of magnesium chips is put in a sonic bath. This solution is added dropwise to a stirred solution of 35.3 ml of diethyloxalate in 70 ml of tetrahydrofuran at -15° C. over 1 hour. The reaction mixture is poured into 3N hydrochloric acid and extracted with methylene chloride. The extract is dried and evaporated. The concentrate is purified by chromatography on silica gel using 5% ethyl acetate:petroleum ether. Fractions containing product are combined and evaporated. The residue is crystallized from petroleum ether to give 21.9 g of the desired product as a solid.

Workup

  1. extractionextracted with methylene chloride
  2. customThe extract is dried
  3. customevaporated
  4. customThe concentrate is purified by chromatography on silica gel using 5% ethyl acetate
  5. additionFractions containing product
  6. customevaporated
  7. customThe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-6e63644d45b445eab617ece4d50f8431
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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