1-Octanethiol → HCID 86743490, compound

HRID 2352665Notes

Reaction equation

HRID 2352665 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]#[C:3][CH3:4].[CH2:8]([SH:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>C1CCN2C(=NCCC2)CC1.CCOCC>[CH2:8]([S:16]/[C:3](/[CH3:4])=[CH:2]/[C:1]([O:6][CH3:7])=[O:5])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 81441-OctanethiolHCID 141019Methyl but-2-ynoate

Product 1

HCID 86743490HCID 86743490, compound

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 3283Diethyl EtherSolvent

Procedure

Two drops of DBU is added to methyl 2-butynoate (6.0 g) under N2. 1-Octanethiol (8.96 g, 61.2 mmol) is added dropwise over 20 min. with cooling with an ice bath. The mixture is allowed to come to RT and is stirred overnight. It is then diluted with ether, washed, dried and stripped and the product is purified by prep. TLC to give methyl (E)-3-octylthio-2butenoate.

Workup

  1. temperaturewith cooling with an ice bath
  2. customto come to RT
  3. washwashed
  4. customdried
  5. customthe product is purified by prep

Sources & evidence

ORD record
ord-a1f4ba846bd343b191d9867d50e08f87
Source dataset
uspto-grants-1989_10
Patent number
US04877899

Reaction notes

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