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

HRID 1769321Notes

Reaction equation

HRID 1769321 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([CH3:18])=[C:9]([C:12]#[C:13][Si](C)(C)C)[CH:10]=2)[S:5][CH2:4][CH2:3]1.[OH-].[K+]>C(O)(C)C>[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([CH3:18])=[C:9]([C:12]#[CH:13])[CH:10]=2)[S:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

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

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 4.4.7-trimethyl-6-trimethylsilylethynylthiochroman, 4 ml of isopropanol and 2.5 ml of aqueous 1N potassium hydroxide was degassed under nitrogen and stirred at room temperature for 16 hours. 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.

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-101f19c8457c46edb0c05f3dcabfacf7
Source dataset
uspto-grants-1995_01
Patent number
US05380877

Reaction notes

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