Tetrahydrofuran → alpha-Ethynyl-4,4-dimethyl-6-thiochromanmethanol

HRID 861771Notes

Reaction equation

HRID 861771 reaction equation
C[Si](C)(C)C#C[CH:5]1[CH2:14][C:13]([CH3:16])([CH3:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:17][OH:18])[CH:11]=2)[S:6]1.[CH2:21]1COC[CH2:22]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:21]([CH:17]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[S:6][CH2:5][CH2:14][C:13]2([CH3:15])[CH3:16])[OH:18])#[CH:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 22361487alpha-Trimethylsilylethynyl-4,4-dimethyl-6-thiochromanmethanol

Product 1

HCID 22619414alpha-Ethynyl-4,4-dimethyl-6-thiochromanmethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.9 g (19.4 mmol) of α-trimethylsilylethynyl-4,4-dimethyl-6-thiochromanmethanol and 50 ml of THF were introduced into a round-bottomed flask and 21.3 ml (23.3 mmol) of a tetrabutylammonium fluoride solution (1.1M in THF) were added dropwise. Stirring was carried out at room temperature for 1 hour and 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 a mixture of ethyl acetate and hexane (1/4). After evaporating the solvents, 3.9 g (87%) of α-ethynyl-4,4-dimethyl-6-thiochromanmethanol were recovered in the form of a colorless 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 a mixture of ethyl acetate and hexane (1/4)
  8. customAfter evaporating the solvents, 3.9 g (87%) of α-ethynyl-4,4-dimethyl-6-thiochromanmethanol
  9. customwere recovered in the form of a colorless oil

Sources & evidence

ORD record
ord-ffb69903eca14c55b97924e710bcf3bd
Source dataset
uspto-grants-1998_02
Patent number
US05716624

Reaction notes

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