Ammonium Chloride → HCID 131735871, compound

HRID 2206881Notes

Reaction equation

HRID 2206881 reaction equation
[CH3:1][O:2][C:3]([O:9][CH3:10])([CH3:8])[C:4](=[N:6][OH:7])[CH3:5].C([Li])CCC.[CH3:16][Si:17]([CH3:31])([CH3:30])[C:18]#[C:19][CH2:20][O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=[O:25].[Cl-].[NH4+]>O1CCCC1>[OH:25][CH:24]([C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[O:21][CH2:20][C:19]#[C:18][Si:17]([CH3:16])([CH3:31])[CH3:30])[CH2:5][C:4](=[N:6][OH:7])[C:3]([O:9][CH3:10])([O:2][CH3:1])[CH3:8]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 131735872HCID 131735872, compoundHCID 131735873HCID 131735873, compoundHCID 178418339Butyllithium

Product 1

HCID 131735871HCID 131735871, compoundYield 127.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,3-dimethoxybutan-2-one oxime (270 mg) in tetrahydrofuran (2.7 ml) was added dropwise, at 0° C. under argon, n-butyllithium (2M in tetrahydrofuran, 1.83 ml). After stirring for a further 5 minutes, a solution of 2-{[3-(trimethylsilyl)prop-2-yn-1-yl]oxy}benzaldehyde (232 mg) in tetrahydrofuran (1 ml) was added dropwise to the reaction mixture, which was stirred for a further 1 hour. Subsequently, concentrated ammonium chloride solution was added to the reaction mixture, and the aqueous phase was removed and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. Purification by column chromatography gave 1-hydroxyl-4,4-dimethoxy-1-(2-{[3-(trimethylsilyl)prop-2-yn-1-yl]oxy}phenyl)pentan-3-one oxime (482 mg, 69%).

Workup

  1. stirringwas stirred for a further 1 hour
  2. customthe aqueous phase was removed
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-b5de9489c8584f7db27b32cb49723289
Source dataset
uspto-grants-2016_06
Patent number
US09375009B2

Reaction notes

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