Potassium Hydroxide → 4,4-Diethyl-6-ethynyl-3,4-dihydro-2H-1-benzothiopyran

HRID 1290056Notes

Reaction equation

HRID 1290056 reaction equation
[OH-].[K+].[CH2:3]([C:5]1([CH2:21][CH3:22])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[C:16][Si](C)(C)C)[CH:13]=2)[S:8][CH2:7][CH2:6]1)[CH3:4]>O.C(O)C>[CH2:21]([C:5]1([CH2:3][CH3:4])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[CH:16])[CH:13]=2)[S:8][CH2:7][CH2:6]1)[CH3:22]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18321988HCID 18321988, compound2×

Product 1

HCID 158953004,4-Diethyl-6-ethynyl-3,4-dihydro-2H-1-benzothiopyran

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.21 g (39 mmol) of potassium hydroxide in 2.0 mL of water and 20.0 mL of ethanol was added to 1.49 g (4.93 mmol) of (4,4-diethylthiochroman-6-yl)(trimethylsilyl)acetylene (Compound 26) and the resulting mixture stirred at room temperature for 5 hours during which time it became homogeneous. The solvent was removed in-vacuo and the residue was acidified with 5% aqueous H2SO4. The product was extracted with 2×50 mL of ether.

Workup

  1. customThe solvent was removed in-vacuo
  2. extractionThe product was extracted with 2×50 mL of ether

Sources & evidence

ORD record
ord-ce9834b53c1f49b98bb79124a5ffa548
Source dataset
uspto-grants-1998_05
Patent number
US05750693

Reaction notes

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