Diethyl Ether → 2-{2-Chloro-1-[(triisopropylsilyl)oxy]ethenyl}pyrimidine

HRID 982728Notes

Reaction equation

HRID 982728 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH:9]([Si:12]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:13][C:14]([C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1)=[CH2:15])([CH3:11])[CH3:10].CCOCC.[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.CCCCCC>[Cl:1][CH:15]=[C:14]([C:16]1[N:17]=[CH:18][CH:19]=[CH:20][N:21]=1)[O:13][Si:12]([CH:9]([CH3:10])[CH3:11])([CH:22]([CH3:24])[CH3:23])[CH:25]([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24083Sulfuric acid magnesium salt (1:1)HCID 31398ChlorosuccinimideHCID 22563218{1-[(Triisopropylsilyl)oxy]vinyl}pyrimidine

Product 1

HCID 858440862-{2-Chloro-1-[(triisopropylsilyl)oxy]ethenyl}pyrimidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

N-chlorosuccinimide (9.97 g, 74.7 mmol) was added to a solution of 2-{1-[(Triisopropylsilyl)oxy]vinyl}pyrimidine (17.3 g, 62.2 mmol) in dry THF (120 ml) under N2 then heated at 65° for 5 hr. After cooling, ether (275 ml) was added and then washed with sat. sodium bicarbonate solution (2×100 ml). The organic layer was dried over sodium sulfate, filtered and evaporated to leave an amber oil. This oil was dissolved in hexane (250 ml), treated with MgSO4 and filtered. Evaporation afforded the product as a yellow oil in quantitative yield.

Workup

  1. temperaturethen heated at 65° for 5 hr
  2. temperatureAfter cooling
  3. washwashed with sat. sodium bicarbonate solution (2×100 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto leave an amber oil
  8. filtrationfiltered
  9. customEvaporation

Sources & evidence

ORD record
ord-a75d848771864bee88aa6e58c660e7e2
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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