Potassium Carbonate → HCID 22991499, compound

HRID 1168117Notes

Reaction equation

HRID 1168117 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[C:9]([CH3:20])[CH:8]=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:6]([C:7]1[CH:19]=[CH:18][C:10]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[C:9]([CH3:20])[CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22991227HCID 22991227, compound

Product 1

HCID 22991499HCID 22991499, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flask equipped with a stirrer and a thermometer, 11.87 g of 2-(4-(trimethylsilylethynyl)-2-methylphenoxy)perhydro-2H-pyrane prepared in Step 2-2 and 0.13 g of potassium carbonate were suspended in 50 g of methanol under a nitrogen atmosphere, stirred at room temperature for 7 hours, and concentrated at 60° C. under a pressure of 20 Torr. The concentrate was purified through silica gel chromatography using a 20/1 (by volume) mixture of hexane/ethylacetate mixed with 0.1 wt % triethyl amine as an eluting solvent, to thereby obtain 8.10 g of 2-(4-ethynyl-2-methylphenoxy)perhydro-2H-pyrane at 91% yield.

Workup

  1. customIn a flask equipped with a stirrer
  2. concentrationconcentrated at 60° C. under a pressure of 20 Torr
  3. customThe concentrate was purified through silica gel chromatography
  4. additiona 20/1 (by volume) mixture of hexane/ethylacetate
  5. additionmixed with 0.1 wt % triethyl amine as an eluting solvent

Sources & evidence

ORD record
ord-3c0fa2514e134e908160b42c1860000d
Source dataset
uspto-grants-2003_09
Patent number
US06623810B2

Reaction notes

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