Triethylamine → HCID 19908458, compound

HRID 1534873Notes

Reaction equation

HRID 1534873 reaction equation
[SH:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[C:7]([OH:14])(=[O:13])/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH3:12].C(N(CC)CC)C>O1CCCC1>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[S:1][CH:9]([CH2:10][CH2:11][CH3:12])[CH2:8][C:7]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5226742-ThiophenethiolHCID 52827072-Hexenoic acid, (2E)-

Product 1

HCID 19908458HCID 19908458, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-mercaptothiophene (51.1 g, 0.44 mol), trans-2-hexenoic acid (1) (49.1 g, 0.43 mol), triethylamine (29.3 g, 0.29 mol) in tetrahydrofuran (490 ml) was stirred and refluxed under nitrogen for 21 hours. The mixture was concentrated in vacuo and the residue was distributed between ethyl acetate (500 ml) and 3N hydrochloric acid (200 ml), the aqueous layer was separated and extracted with ethyl acetate (200 ml), the combined ethyl acetate extracts were washed with 3N hydrochloric acid, twice with water and dried over sodium sulfate. The solvent was evaporated in vacuo to yield pale yellow oily product weighing 99 g (100%), which was >96% pure by HPLC.

Workup

  1. temperaturerefluxed under nitrogen for 21 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe aqueous layer was separated
  4. extractionextracted with ethyl acetate (200 ml)
  5. washthe combined ethyl acetate extracts were washed with 3N hydrochloric acid, twice with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customto yield pale yellow oily product

Sources & evidence

ORD record
ord-e2ab5a82dd424f9d8f489a22c6703ff5
Source dataset
uspto-grants-1992_02
Patent number
US05091409

Reaction notes

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