Hydrochloric Acid → (S)-3-hex-5-enylsulfanyl-2-methyl-propionic acid

HRID 1432101Notes

Reaction equation

HRID 1432101 reaction equation
[C:1]([S:4][CH2:5][C@@H:6]([CH3:10])[C:7]([OH:9])=[O:8])(=O)[CH3:2].[OH-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17]C=C.Cl>CO.CCOC(C)=O>[CH2:1]([S:4][CH2:5][C@@H:6]([CH3:10])[C:7]([OH:9])=[O:8])[CH2:2][CH2:17][CH2:16][CH:15]=[CH2:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 759066-Bromo-1-hexeneHCID 2724506D-beta-acetylthioisobutyric acid

Product 1

HCID 86611584(S)-3-hex-5-enylsulfanyl-2-methyl-propionic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.62 g (10 mmol) (S)-3-acetylsulfanyl-2-methyl-propionic acid in 20 ml MeOH is treated with 7.5 ml 4N NaOH and 1.63 g (10 mmol) 6-bromo-hex-1-ene. After being stirred for 1 h at rt the mixture is diluted with 50 ml EtOAc and acidified with 25 ml 1N HCl. The organic phase is washed with brine, dried with sodium sulfate and concentrated in vacuo to yield (S)-3-hex-5-enylsulfanyl-2-methyl-propionic acid as an oil which is used without purification for the next step.

Workup

  1. washThe organic phase is washed with brine
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d0a35cfe797481585345ba553764e3f
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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