Trichloroethanol → HCID 17979073, compound

HRID 1354137Notes

Reaction equation

HRID 1354137 reaction equation
[H-].[Na+].[Cl:3][C:4]([Cl:8])([Cl:7])[CH2:5][OH:6].Cl[C:10]1[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=1.[CH2:17]([OH:21])[C:18]#[C:19][CH3:20].[Cl-].[NH4+]>O1CCCC1>[CH2:17]([O:21][C:10]1[CH:15]=[C:14]([O:6][CH2:5][C:4]([Cl:8])([Cl:7])[Cl:3])[N:13]=[CH:12][N:11]=1)[C:18]#[C:19][CH3:20]

Participants

7

Reactant 5

HCID 8259TrichloroethanolHCID 129912-Butyn-1-olHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 17979073HCID 17979073, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.30 g of 2,2,2-trichloro ethanol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 2 hours. To this was added dropwise 0.4 ml of a solution containing 0.17 g of 2-butyn-1-ol at room temperature and further added 0.11 g of sodium hydride (60% in oil), followed by stirring for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.20 g of 4-(2-butynyloxy)-6-(2,2,2-trichloroethyloxy)pyrimidine (the present compound (35)).

Workup

  1. additionwas added dropwise at 0° C.
  2. stirringby stirring at the same temperature for 2 hours
  3. stirringby stirring for 3 hours
  4. extractionwas extracted three times with t-butyl methyl ether
  5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9fd5ded3511e4a8192f2e5d5b2eb3c2d
Source dataset
uspto-grants-2007_05
Patent number
US07223769B2

Reaction notes

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