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

HRID 1376804Notes

Reaction equation

HRID 1376804 reaction equation
[OH-].[K+].O.[CH2:4]([C:6]1([CH2:22][CH3:23])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[C:17][Si](C)(C)C)[CH:14]=2)[S:9][CH2:8][CH2:7]1)[CH3:5]>C(O)C>[CH2:22]([C:6]1([CH2:4][CH3:5])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[CH:17])[CH:14]=2)[S:9][CH2:8][CH2:7]1)[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 18321988HCID 18321988, compound2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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-b19fcb5f58cc4145b0eceffabf455666
Source dataset
uspto-grants-1997_09
Patent number
US05663347

Reaction notes

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