Ammonium Acetate → {4-[4-Ethoxy-3-methyl-3-(methylsulfonyl)-4-oxobutyl]phenyl}boronic acid

HRID 533546ノート

反応式

HRID 533546 の反応式
[CH3:1][C:2]([S:25]([CH3:28])(=[O:27])=[O:26])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([B:16]2[O:20]C(C)(C)C(C)(C)[O:17]2)=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])(=O)C.[NH4+].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.Cl>[CH2:6]([O:5][C:3](=[O:4])[C:2]([CH3:1])([S:25]([CH3:28])(=[O:26])=[O:27])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([B:16]([OH:20])[OH:17])=[CH:12][CH:11]=1)[CH3:7]

参加物

6

反応物 3

HCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 66578081Ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate

生成物 1

HCID 66577887{4-[4-Ethoxy-3-methyl-3-(methylsulfonyl)-4-oxobutyl]phenyl}boronic acid

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 313Hydrochloric Acid溶媒

実験手順

To a solution of ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate, which may be prepared as in Preparation Number 3, Step A, (4.75 g, 11.5 mmol) in acetone (90 mL) was added ammonium acetate (0.1 M in water, 232 mL, 23.2 mmol) and sodium periodate (7.43 g, 34.7 mmol). The mixture was stirred at ambient temperature overnight. The mixture was diluted with 1N HCl aq. and extracted with ether 2×. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo to give {4-[4-ethoxy-3-methyl-3-(methylsulfonyl)-4-oxobutyl]phenyl}boronic acid as an orange oil 3.44 g. LCMS: (M+1) 329.2

後処理

  1. extractionextracted with ether 2×
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0ef9bc9825fa47d3a02c8f5d53477f92
出典データセット
uspto-grants-2014_10
特許番号
US08853258B2

反応ノート

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