Isobutanol → HCID 66602888, compound

HRID 2097540Notes

Reaction equation

HRID 2097540 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([OH:10])[CH:7]([CH3:9])[CH3:8].[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(=O)C=2C=1CBr>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]([CH3:28])([CH3:29])[CH3:30])[C:5](=[O:1])[C:4]=2[C:3]=1[CH2:2][O:10][CH2:6][CH:7]([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 6560IsobutanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 66602679HCID 66602679, compound

Product 1

HCID 66602888HCID 66602888, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 ml of dehydrated tetrahydrofuran solution containing 1 ml of isobutanol was added 0.49 g of sodium hydride (60% dispersed material in mineral oil) under cooling in ice-bath, and the mixture was stirred at room temperature for 15 minutes. Then, 0.99 g (1.75 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 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 0.66 g of the title compound as a colorless oil. (Yield: 67%)

Workup

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

Sources & evidence

ORD record
ord-ca7c1068671d430499173e88e986d8b0
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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