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

HRID 6542Notes

Reaction equation

HRID 6542 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 73) 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): δ 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) The solvent
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-fd81178d17144eccb85427ba5786701d
Source dataset
uspto-grants-1993_09
Patent number
US05248777

Reaction notes

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