Barium hydroxide → N-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]-2-aminoethanol

HRID 1023985ノート

反応式

HRID 1023985 の反応式
[CH2:1]([O:8][C:9]1[CH:28]=[C:27]([CH2:29][CH3:30])[CH:26]=[CH:25][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH2:21][O:20]C2=O)=[CH:14][C:13]=1[F:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Ba+2].[OH-]>CO.O>[CH2:1]([O:8][C:9]1[CH:28]=[C:27]([CH2:29][CH3:30])[CH:26]=[CH:25][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:22][CH2:21][OH:20])=[CH:14][C:13]=1[F:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 6093286Barium hydroxideHCID 591913503-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]oxazolidin-2-one

生成物 1

HCID 59191271N-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]-2-aminoethanol収率 92.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

To a solution of 3-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]oxazolidin-2-one (350 mg, 0.85 mmol) in 5 ml of methanol was added barium hydroxide (245 mg, 1.28 mmol) taken in 5 ml of water. The reaction mixture was warmed to 65° C. and stirred overnight (reaction was complete on TLC). The reaction mixture concentrated in vacuo to remove methanol, diluted with water and the aqueous layer was extracted with ethyl acetate. The combined organic fraction was washed with brine, dried over anhydrous Na2SO4 and concentrated to get 300 mg, 91.57% of the title compound as a brown oil, used as such in the next step.

後処理

  1. custom(reaction was complete on TLC)
  2. concentrationThe reaction mixture concentrated in vacuo
  3. customto remove methanol
  4. additiondiluted with water
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic fraction was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3c59ef4dec25467ea4c7eded8abf63d0
出典データセット
uspto-grants-2014_05
特許番号
US08722746B2

反応ノート

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