Water → HCID 58452409, compound

HRID 70515Notes

Reaction equation

HRID 70515 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:12]([C:14]2[CH:24]=[CH:23][C:17]3[N:18]([CH3:22])[CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)[OH:13])=[N:8][C:9]=1[O:10][CH3:11].O>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:12]([C:14]2[CH:24]=[CH:23][C:17]3[N:18]([CH3:22])[CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)=[O:13])=[N:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 67396961HCID 67396961, compound

Product 1

HCID 58452409HCID 58452409, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (purity: 63%, 75 mg) was added to a solution of (5-chloro-6-methoxypyridin-2-yl)(4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)methanol (302 mg) in tetrahydrofuran (2 mL) under ice-cooling, and the mixture was stirred with warming to room temperature overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1) to give the title compound as a yellow solid (231 mg).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-ed5d8e61dfdc4df2844531dbcee5630e
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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