Isopropanol → HCID 14744866, compound

HRID 2226344Notes

Reaction equation

HRID 2226344 reaction equation
[CH2:1]([C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=[CH2:32])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[SiH:34]([CH3:36])[CH3:35].[CH:37](O)(C)C>>[CH2:1]([C:9]1[CH:14]=[N:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][Si:34]([CH3:36])([CH3:37])[CH3:35])=[CH:17][CH:16]=2)=[N:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 66108ChlorodimethylsilaneHCID 14439129HCID 14439129, compound

Product 1

HCID 14744866HCID 14744866, compound

Procedure

2 g (4.6 mmol) of 10-undecenyl 4-(5-octylpyrimidin-2-yl)phenyl ether, 6 g (63.4 mmol) of chlorodimethylsilane and 0.1 ml of a 0.1 molar solution of H2PtCl6 in isopropanol are heated at 100° C. for 8 h in a sealed glass tube. After opening the tube, the product is evaporated down, taken up in 10 ml of dry tetrahydrofuran and mixed with 50 ml of a 1 molar solution of methylmagnesium bromide in tetrahydrofuran. After heating for 2 hours under reflux, the mixture is hydrolyzed in a saturated aqueous NH4Cl solution and the aqueous solution is extracted repeatedly with diethyl ether. The combined organic phases are washed with saturated NaCl solution, dried over MgSO4 and evaporated down in vacuo. After chromatographic purification (SiO2, CH2Cl2 /hexane 3/1) and recrystallization from methanol, 700 mg of colorless crystals are obtained.

Workup

  1. customthe product is evaporated down
  2. additionmixed with 50 ml of a 1 molar solution of methylmagnesium bromide in tetrahydrofuran
  3. temperatureAfter heating for 2 hours
  4. temperatureunder reflux
  5. extractionthe aqueous solution is extracted repeatedly with diethyl ether
  6. washThe combined organic phases are washed with saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. customevaporated down in vacuo
  9. customAfter chromatographic purification (SiO2, CH2Cl2 /hexane 3/1) and recrystallization from methanol, 700 mg of colorless crystals
  10. customare obtained

Sources & evidence

ORD record
ord-c0378479404a41b5a868da2c61240408
Source dataset
uspto-grants-1994_09
Patent number
US05348684

Reaction notes

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