Potassium Hydroxide → 4,4,7-Trimethyl-6-ethynylthiochroman

HRID 6537Notes

Reaction equation

HRID 6537 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[S:13][CH2:12][CH2:11][C:10]2([CH3:19])[CH3:18])(C)C.[OH-].[K+]>C(O)(C)C>[CH3:18][C:10]1([CH3:19])[C:9]2[C:14](=[CH:15][C:16]([CH3:17])=[C:7]([C:6]#[CH:5])[CH:8]=2)[S:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15661126Trimethylsilyl (4,4,7-trimethyl-thiochroman-6-yl) ethyne2×

Product 1

HCID 156611284,4,7-Trimethyl-6-ethynylthiochroman

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 380 mg (1.69 mmol of trimethylsilyl (4,4,7-trimethyl-thiochroman-6-yl) ethyne, (Compound 67) 4 ml of isopropanol and 2.5 ml of aqueous 1N potassium hydroxide was degassed under nitrogen and stirred at room temperature for 16 h. The mixture was concentrated under vacuum and extracted with 2×10 ml of ether. The ether extracts were combined and 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 1.31 (6H, s), 1.88-1.96 (2H, m), 2.35 (3H, s), 3.00-3.08 (2H, m), 3.25 (1H, s), 6.94 (1H, s), 7.47 (1H, s).

Workup

  1. customwas degassed under nitrogen
  2. concentrationThe mixture was concentrated under vacuum
  3. extractionextracted with 2×10 ml of ether
  4. washwashed successively with water and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c6412dfebb444e2990d8e868c7d27f9b
Source dataset
uspto-grants-1993_09
Patent number
US05248777

Reaction notes

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