(+-)-2-Butanol → HCID 66602290, compound

HRID 2097541Notes

Reaction equation

HRID 2097541 reaction equation
O1CCCC1.[CH3:6][CH:7]([OH:10])[CH2:8][CH3:9].[H-].[Na+].[Br:13][C:14]1[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:17]2[CH:18]=[N:19][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:21](=[O:22])[C:16]=2[C:15]=1[CH2:40]Br>O>[Br:13][C:14]1[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:17]2[CH:18]=[N:19][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:21](=[O:22])[C:16]=2[C:15]=1[CH2:40][O:10][CH:7]([CH2:8][CH3:9])[CH3:6]

Participants

6

Reactant 4

HCID 6568(+-)-2-ButanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 66602679HCID 66602679, compound

Product 1

HCID 66602290HCID 66602290, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4 ml of dehydrated tetrahydrofuran solution containing 0.96 ml of 2-butanol was added 0.30 g of sodium hydride (60% dispersed material in mineral oil), and the mixture was stirred at room temperature for 3 hours. Then, 0.85 g (1.50 mmol) of 2-bromo-3-bromomethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 25-(a) was added to the mixture under cooling in ice-bath, and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed successively with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1→4:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 0.46 g of the title compound as a colorless oil. (Yield: 55%)

Workup

  1. addition25-(a) was added to the mixture
  2. temperatureunder cooling in ice-bath
  3. stirringthe mixture was stirred at the same temperature for 1 hour
  4. additionwas added to the reaction mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. customThe organic layer after separation
  7. washwas washed successively with water
  8. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionthe fractions containing the desired compound
  11. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-883935e41dd94e1087262a533049ff76
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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