Hydrochloric Acid → HCID 68139102, compound

HRID 1076978Notes

Reaction equation

HRID 1076978 reaction equation
CCCC[O-].[Na+].Cl[CH2:8][CH:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[NH:16][CH:15]=3)[NH:11][CH2:10]1.Cl>>[CH2:8]=[C:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[NH:16][CH:15]=3)[NH:11][CH2:10]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 23669364Sodium n-butylateHCID 68138577HCID 68138577, compound

Product 1

HCID 68139102HCID 68139102, compound

Procedure

To date, only one 8-alkoxymethylergoline has been prepared and isolated. In particular, Zikan and Semonsky prepared D6-methyl-8-n-butoxymethylergoline by reaction of sodium butylate and the corresponding 8-chloromethylergoline. These workers reported that the reaction, when carried out with most sodium alcoholates, led primarily to elimination of hydrochloric acid and provided the corresponding 8-methylenergoline derivative; see Coll. Czech. Chem. Comm. 39, 614 (1974). Indeed, reaction of D-6-methyl-8-chloromethylergoline with sodium methoxide under the conditions taught by Zikan and Semonsky, effected only elimination of the elements of hydrochloric acid, affording exclusively the corresponding 8-methylenergoline.

Workup

  1. customisolated
  2. customIn particular, Zikan and Semonsky prepared D6-methyl-8-n-butoxymethylergoline
  3. customThese workers reported that the reaction, when

Sources & evidence

ORD record
ord-24d62dfb5c7945edab8c62f84630f9b4
Source dataset
uspto-grants-1976_05
Patent number
US03959288

Reaction notes

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