Sodium Thiosulfate → Methyl 2-(3-bromophenyl)-2-oxoacetate

HRID 547106ノート

反応式

HRID 547106 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:13][Si](C=[N+]=[N-])(C)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C1C=CC=CC=1.CO>[CH3:13][O:10][C:9](=[O:11])[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:12]

参加物

8

反応物 5

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium BicarbonateHCID 27570282-(3-Bromophenyl)-2-hydroxyacetic acid

生成物 1

HCID 11615668Methyl 2-(3-bromophenyl)-2-oxoacetate収率 95%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 887Methanol溶媒

実験手順

(3-Bromo-phenyl)-hydroxy-acetic acid (526.4 mg, 2.23 mmol) was dissolved in benzene (6 mL) and methanol (3 mL). Trimethylsilyldiazomethane (2 M solution in diethyl ether, 1.23 mL, 2.46 mmol) was added, and the mixture was stirred at room temperature for 10 minutes. The reaction solution was concentrated under reduced pressure, and then the residue was dissolved in dichloromethane (11.2 mL). Dess-Martin periodinane (1.95 g, 4.47 mmol) was added, and the mixture was stirred at room temperature for 10 minutes. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and brine and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 85:15) to give the title compound (502.2 mg, 95% in two steps).

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (11.2 mL)
  3. stirringthe mixture was stirred at room temperature for 10 minutes
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 85:15)

出典と根拠

ORDレコード
ord-c180ef816be549159b1606ba79db49a5
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

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