Potassium Hydroxide → HCID 57249165, compound

HRID 1761463Notes

Reaction equation

HRID 1761463 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]([CH:7]1[CH:21]=[C:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][CH:13]=3)[NH:9][CH2:8]1)=[O:6].Cl[C:24]([O:26][CH2:27][C:28]([Cl:31])([Cl:30])[Cl:29])=[O:25].[C:32](=[O:35])(O)[O-:33].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:3][O:4][C:5]([CH:7]1[CH:21]=[C:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[N:14]([C:24]([O:26][CH2:27][C:28]([Cl:31])([Cl:30])[Cl:29])=[O:25])[CH:13]=3)[N:9]([C:32]([O:33][CH2:27][C:28]([Cl:31])([Cl:30])[Cl:29])=[O:35])[CH2:8]1)=[O:6]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 57009830HCID 57009830, compound

Product 1

HCID 57249165HCID 57249165, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

30 g of pulverized potassium hydroxide is added to a solution of 7.65 g of 9,10-didehydroergoline-8-carboxylic acid methyl ester (28.5 mmol) and 1.22 g of tetrabutylammonium hydrogen sulfate in 900 ml of methylene chloride, and then 125 ml of trichloroethyl chloroformate is added dropwise thereto. After 15 minutes, the mixture is cooled in an ice bath, gently combined with about 300 ml of saturated sodium bicarbonate solution, and stirred for one hour. After extraction with chloroform, this phase is washed with water, dried over magnesium sulfate, and evaporated. The crude product is chromatographed on silica gel with chloroform and methanol, yielding 13.85 g (79% of theory) of 9,10-didehydro-1,6-bis(2,2,2-trichloroethoxycarbonyl)-8-ergolinecarboxylic acid methyl ester as an oily mixture of isomers.

Workup

  1. temperaturethe mixture is cooled in an ice bath
  2. extractionAfter extraction with chloroform
  3. washthis phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe crude product is chromatographed on silica gel with chloroform and methanol

Sources & evidence

ORD record
ord-54902fdababd4600bdc7cb87c90b0708
Source dataset
uspto-grants-1989_05
Patent number
US04826852

Reaction notes

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