Tetrahydrofuran → 6-Ethynyl-4,4-dimethylthiochroman

HRID 861782Notes

Reaction equation

HRID 861782 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[S:10][CH2:9][CH2:8][C:7]2([CH3:15])[CH3:14].C1COCC1.C([Li])CCC>O>[CH3:14][C:7]1([CH3:15])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([C:3]#[CH:2])[CH:5]=2)[S:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 226194372,2-Dibromo-1-(4,4-dimethylthiochroman-6-yl)ethyleneHCID 178418339Butyllithium

Product 1

HCID 109325396-Ethynyl-4,4-dimethylthiochroman

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.7 g (21.2 mmol) of 2,2-dibromo-1-(4,4-dimethylthiochroman-6-yl)ethylene and 80 ml of THF were introduced into a three-necked flask under a stream of nitrogen. 17 ml (26.6 mmol) of an n-butyllithium solution (2.5M in hexane) were added dropwise at -78° C. and the mixture was permitted to heat to room temperature for one hour. The reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with heptane. 3.9 g (90%) of the expected acetylene derivative were recovered in the form of a yellow oil.

Workup

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica column
  7. washeluted with heptane
  8. custom3.9 g (90%) of the expected acetylene derivative were recovered in the form of a yellow oil

Sources & evidence

ORD record
ord-6eef5ddd781b411e91f1fae5751c4929
Source dataset
uspto-grants-1998_02
Patent number
US05716624

Reaction notes

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