Potassium Hydroxide → 2,2,4,4-Tetramethyl-6-ethynylthiochroman

HRID 2081357Notes

Reaction equation

HRID 2081357 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]#[C:15][Si](C)(C)C)[CH:8]=2)[S:3]1.[OH-].[K+]>C(O)(C)C>[CH3:1][C:2]1([CH3:20])[CH2:11][C:10]([CH3:12])([CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]#[CH:15])[CH:8]=2)[S:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 156611272,2,4,4-Tetramethyl-6-trimethylsilylethynylthiochroman

Product 1

HCID 156611292,2,4,4-Tetramethyl-6-ethynylthiochroman

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 527.6 mg (1.75 mmol) of 2,2,4,4-tetramethyl-6-trimethylsilyl-ethynylthiochroman (Compound 34) in 4 ml of isopropanol was added, under argon, 4 ml of 1N KOH solution. The reaction mixture was stirred at room temperature for 20 h and the isopropanol was then removed under vacuum. The residue was extracted with ether and the combined ether extracts were washed successively with water and saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo to give the title compound as a yellow oil. PMR (CDCl3): & 1.34 (6H, s), 1.37 (6H, s), 1.91 (2H, s), 2.99 (1H, s), 7.17 (1H, dd, J~8.1 Hz, 1.8 Hz), 7.26 (1H, d, J~1.8 Hz), 7.30 (1H, d, J~8.1 Hz). MS exact mass, m/e 230.1122 (calcd. for C15H18S, 230.1129)

Workup

  1. customthe isopropanol was then removed under vacuum
  2. extractionThe residue was extracted with ether
  3. washthe combined ether extracts were washed successively with water and saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3b1b28d3b46f4e84a30e8e07f00c1062
Source dataset
uspto-grants-1993_02
Patent number
US05183827

Reaction notes

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