Ammonium Chloride → Ethyl 8-acetyl-12-(acetyloxy)-8-methylheptadecanoate

HRID 1730226Notes

Reaction equation

HRID 1730226 reaction equation
[I-].[CH3:2][Li].[C:4]([C:7](Br)([CH2:19][CH2:20][CH2:21][CH:22]([O:28][C:29](=[O:31])[CH3:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:6])[CH3:5].[Cl-].[NH4+]>CCOCC>[C:4]([C:7]([CH3:2])([CH2:19][CH2:20][CH2:21][CH:22]([O:28][C:29](=[O:31])[CH3:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:6])[CH3:5]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 30165Iodide IonHCID 21397377Ethyl 8-acetyl-12-(acetyloxy)-8-bromoheptadecanoateHCID 178418348HCID 178418348, compound

Product 1

HCID 21397375Ethyl 8-acetyl-12-(acetyloxy)-8-methylheptadecanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Cupruous iodide (7.1 g., 0.037 mole) is suspended in ether (150 ml.) and a 1.66 M solution of methyl lithium in ether (45 ml., 0.075 mole) is added dropwise during 30 minutes. Ethyl 8-acetyl-8-bromo-12-acetoxyheptadecanoate (11.9 g., 0.025 mole) is added dropwise during 30 minutes. The temperature is kept at -4° C to -2° C. during these operations by means of a salt bath. Stirring is continued at this temperature for another 30 minutes; then the mixture is stirred for 2 hours without cooling. The reaction mixture is then treated with 200 ml. of saturated ammonium chloride solution. The organic layer is separated, washed with brine and dried over sodium sulfate. Distillation of the solvent in vacuo leaves the crude product as an orange oil weighing 9.2 g. The product is purified by column chromatography using 250 g. of silica gel and chloroform as the eluant. Ethyl 8-acetyl-8-methyl-12-acetoxyheptadecanoate is obtained as yellow viscous oil.

Workup

  1. customThe temperature is kept at -4° C to -2° C. during these operations by means of a salt bath
  2. stirringthen the mixture is stirred for 2 hours
  3. temperaturewithout cooling
  4. additionThe reaction mixture is then treated with 200 ml
  5. customThe organic layer is separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. distillationDistillation of the solvent in vacuo
  9. customleaves the crude product as an orange oil
  10. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-4643de0cbfc3407397c202187cab33fc
Source dataset
uspto-grants-1976_11
Patent number
US03991087

Reaction notes

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