Triethylamine → HCID 22991227, compound

HRID 1168116Notes

Reaction equation

HRID 1168116 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)=[C:4]([CH3:15])[CH:3]=1.C(N(CC)CC)C.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>C(OC(=O)C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:23][Si:24]([C:27]#[C:28][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)=[C:4]([CH3:15])[CH:3]=1)([CH3:26])[CH3:25]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 22991646HCID 22991646, compound

Product 1

HCID 22991227HCID 22991227, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
58 °C

Procedure

In a flask equipped with a stirrer and a thermometer, 13.36 g of 1-iodo-4-perhydro-2H-pyrane-2-yloxy-3-methylbenzene prepared in Step 2-1, 0.24 g of dichlorobis(triphenylphosphine)palladium, 0.24 g of triphenylphosphine, 0.12 g of copper iodide (I), and 12.75 g of triethyl amine were suspended in 50 g of ethylacetate under a nitrogen atmosphere, and heated up to 58° C. under stirring. Then a solution of 6.20 g of trimethylsilylacetylene and 6.20 g of ethylacetate was added dropwise at 58 to 64° C. over 2 hours. The resulting mixture was stirred at the same temperature for 3 hours, cooled down to room temperature, and filtered. The residue was washed with ethylacetate, and the resulting filtrate was concentrated at 60° C. under a pressure of 20 Torr. The concentrate was purified through silica gel chromatography using hexane mixed with 0.1 wt % triethyl amine as an eluting solvent, to thereby obtain 11.87 g of 2-(4-(trimethylsilylethynyl)-2-methylphenoxy)perhydro-2H-pyrane at 98% yield.

Workup

  1. customIn a flask equipped with a stirrer
  2. stirringThe resulting mixture was stirred at the same temperature for 3 hours
  3. temperaturecooled down to room temperature
  4. filtrationfiltered
  5. washThe residue was washed with ethylacetate
  6. concentrationthe resulting filtrate was concentrated at 60° C. under a pressure of 20 Torr
  7. customThe concentrate was purified through silica gel chromatography
  8. additionmixed with 0.1 wt % triethyl amine as an eluting solvent

Sources & evidence

ORD record
ord-9706b751c7b743bdbfe4db673c012f48
Source dataset
uspto-grants-2003_09
Patent number
US06623810B2

Reaction notes

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