Methyl 3-mercaptopropionate → HCID 20462179, compound

HRID 326107Notes

Reaction equation

HRID 326107 reaction equation
BrCCCCCCCCCCCO.C([O-])CCCCC.[Na+].P(Br)(Br)Br.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].[SH:45][CH2:46][CH2:47][C:48](OC)=[O:49].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C[O-].[Na+].N1C=CC=CC=1>[CH2:39]([O:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][S:45][CH2:46][CH2:47][CH2:48][OH:49])[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

9

Reactant 6

HCID 18050Methyl 3-mercaptopropionateHCID 24614Phosphorus tribromideHCID 7416311-Bromo-1-undecanolHCID 20462175HCID 20462175, compoundHCID 21226445Aluminium lithium hydrideHCID 236936241-Hexanol, sodium salt (1:1)

Product 1

HCID 20462179HCID 20462179, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 10942334Sodium MethoxideSolvent

Procedure

11-Bromoundecan-1-ol (m.p. 45°-48° C. ) is reacted with sodium hexanolate and the syrupy product obtained is reacted with phosphorus tribromide in the presence of pyridine. The structure of the oil obtained is confirmed by mass spectroscopy as being 11-bromoundecyloxyhexane. This bromo compound is reacted with methyl β-mercaptopropionate in sodium methylate solution and the oil obtained is then reduced with lithium aluminium hydride to give 3-(11-hexyloxyundecylthio)-propanol; m.p. 27°-29° C. Phosphorylation and choline ester formation in a manner analogous to that described in Example 20C gives the desired end product in a yield of 55% of theory in the form of a monohydrate which sinters at 98° C. and decomposes at 226°-229° C.

Workup

  1. customthe syrupy product obtained
  2. customThe structure of the oil obtained
  3. customthe oil obtained

Sources & evidence

ORD record
ord-14e774b6cda84077bd52635928c7a7db
Source dataset
uspto-grants-1984_04
Patent number
US04444766

Reaction notes

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