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Diethyl Ether → (+)-β-Amino-3,4-difluoro-α,α-dimethylbenzeneethanol

HRID 1832158
ノート
印刷プレビュー

反応式

HRID 1832158 の反応式
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[CH:8]=1)C(OC)=O.[CH3:15][Mg]Br.[Cl-].[NH4+].CC[O:22][CH2:23][CH3:24]>>[F:14][C:9]1[CH:8]=[C:7]([CH:2]([NH2:1])[C:23]([CH3:24])([OH:22])[CH3:15])[CH:12]=[CH:11][C:10]=1[F:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 3283Diethyl Ether2 回HCID 25517Ammonium ChlorideHCID 22049608Methyl 2-amino-2-(3,4-difluorophenyl)acetateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 18623229(+)-β-Amino-3,4-difluoro-α,α-dimethylbenzeneethanol収率 62%

反応条件

温度
0 °C

実験手順

Into a well-stirred solution of methyl 2-amino-2-(3,4-difluorophenyl)acetate (10.5 g, 52.19 mmol) in anhydrous ether (200 mL) at 0° C. a solution of methylmagnesium bromide (3 M, 87 mL, 261 mmol) in ether was added over 10 minutes. The reaction mixture was stirred at 0° C. for 2.5 h and allowed to warm to room temperature. After 12 h, the reaction mixture was carefully poured onto a mixture of ice (300 g) and saturated aqueous ammonium chloride (50 g). The ether layer was separated and the aqueous layer was extracted with more ether (4×200 mL). The combined extracts were dried with magnesium sulfate and the solvent evaporated. The crude product was purified by column chromatography on silica gel using chloroform/methanol/2M ammonia in methanol (1000:20:10, 1000:40:20, 1000:80:40) as the eluent to give the product as an oil (6.5 g, 62% yield) which was used in the next step without further purification.

後処理

  1. temperatureto warm to room temperature
  2. waitAfter 12 h
  3. customThe ether layer was separated
  4. extractionthe aqueous layer was extracted with more ether (4×200 mL)
  5. dry with materialThe combined extracts were dried with magnesium sulfate
  6. customthe solvent evaporated
  7. customThe crude product was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-7ddb65a92df744959f9345716a361b75
出典データセット
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07067534B1

反応ノート

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