Potassium Carbonate → 6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

HRID 841563Notes

Reaction equation

HRID 841563 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][Si](C)(C)C)[CH:10]=2)[C:5](=[O:18])[CH2:4][CH2:3]1.CC1(C)C2C(=CC=C([Si](C)(C)C)C=2)C(=O)C(C#C)C1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5](=[O:18])[CH2:4][CH2:3][C:2]2([CH3:19])[CH3:1])#[CH:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 225688166-(trimethylsilyl)ethynyl-3,4-dihydro-4,4-dimethyl-naphthalen-1(2H)-oneHCID 865859204,4-Dimethyl-6-trimethylsilanyl-ethynyl-1,2,3,4-tetrahydronaphthalene-1-one

Product 1

HCID 225688236-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-oneYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4,4-dimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydronaphthalene-1-one (Intermediate 12, 0.28 g, 1.03 mmol) in methanol (10 mL was treated with potassium carbonate (0.74 g, 5.35 mmol) and stirred at ambient temperature for 4 h. The volatiles were distilled off in vacuo and the residue was diluted with water and extracted with diethyl ether (×2). The combined organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound (0.19 g, 89%) as an oil that solidified on standing.

Workup

  1. distillationThe volatiles were distilled off in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether (×2)
  4. extractionThe combined organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-deb6d36b0b774609830104d948edf661
Source dataset
uspto-grants-2002_04
Patent number
US06369261B1

Reaction notes

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