Potassium Hydroxide → HCID 18966362, compound

HRID 2226177Notes

Reaction equation

HRID 2226177 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1.[OH-].[K+]>C(O)(C)C>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18966566HCID 18966566, compound2×

Product 1

HCID 18966362HCID 18966362, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1 g (3.6 mmol) of 4,4-dimethyl-7-trimethylsilylethynyl-thio-chroman (Compound 47) in 10 ml of isopropyl alcohol was added 5 ml of 1N KOH solution. The reaction mixture was stirred at room temperature for 18 hours and the isopropanol was then removed under vacuum. The residue was extracted with ether and the ether extracts were combined and washed with dilute HCl solution, water and saturated NaCl solution, and were thereafter dried (MgSO4). The solvent was removed in vacuo to give impure 4-4-dimethyl-7-ethynyl-thiochroman (Compound 48) as a pale yellow oil. This mixture was used in the next step without further purification. A solution of 281 mg of this impure 4,4-dimethyl-7-ethynylthiochroman (Compound 48) and 384 mg (1.4 mmol) of ethyl 4-iodo-benzoate in 1 ml of triethylamine was placed in a heavy walled glass tube and degassed under nitrogen. The mixture was treated with 60 mg of cuprous iodide and 30 mg of bis (triphenyl phosphine) palladium (II) chloride. The reaction mixture was degassed again under nitrogen, and the tube was sealed. The reaction mixture was stirred at room temperature for 18 hours. The solvent was removed under high vacuum and the residue purified by flash column chromatography (silica; 3% EtOAC/hexane) to give the title compound as an off-white solid.

Workup

  1. customthe isopropanol was then removed under vacuum
  2. extractionThe residue was extracted with ether
  3. washwashed with dilute HCl solution, water and saturated NaCl solution
  4. dry with materialwere thereafter dried (MgSO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d9327f21cb0342bdaae52a908f672fdf
Source dataset
uspto-grants-1994_09
Patent number
US05346915

Reaction notes

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