Tetrabutylammonium Fluoride → (E)-4-(3,4-dichlorophenyl)but-3-en-1-ol

HRID 1771085ノート

反応式

HRID 1771085 の反応式
C([Si]([O:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)(C)C)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[Cl:20][C:15]1[CH:14]=[C:13](/[CH:12]=[CH:11]/[CH2:10][CH2:9][OH:8])[CH:18]=[CH:17][C:16]=1[Cl:19]

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 86728169HCID 86728169、化合物

生成物 1

HCID 86728170(E)-4-(3,4-dichlorophenyl)but-3-en-1-ol収率 97%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To solution of Intermediate 2A (2.2 g, 5.2 mmol) in THF (50 mL) cooled to 0° C. was added TBAF (6.3 mL, 6.3 mmol) via dropwise addition. The reaction mixture was stirred at 0° C. for 1 h, then diluted with ethyl acetate (200 mL). The organic layer was washed with water (2×100 mL), dried over Na2SO4 and dried in vacuo. The product was purified by silica gel chromatography (80 g silica gel; linear gradient 0-25% ethyl acetate for 30 min) to obtain 917 mg (97% yield) of Intermediate 2B. HPLC/MS (Method D) RT=1.00 min, [M−H2O+1]+ 199.1.

後処理

  1. additionvia dropwise addition
  2. washThe organic layer was washed with water (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. customdried in vacuo
  5. customThe product was purified by silica gel chromatography (80 g silica gel; linear gradient 0-25% ethyl acetate for 30 min)

出典と根拠

ORDレコード
ord-d34954c53e7e46e28839ad3664cf82ae
出典データセット
uspto-grants-2016_02
特許番号
US09249096B2

反応ノート

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