2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol

HRID 1499590ノート

反応式

HRID 1499590 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:9]([OH:12])([CH3:11])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[Li]CCCC.C(O[B:22]1[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]1)(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]([OH:12])([CH3:10])[CH3:11])[CH:5]=[C:6]([F:8])[C:7]=1[B:22]1[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]1

参加物

5

反応物 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 577321592-(3,5-Difluorophenyl)propan-2-olHCID 178418339Butyllithium

生成物 1

HCID 706551562-(3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 2-(3,5-difluorophenyl)propan-2-ol (2.00 g, 11.6 mmol) in THF (46 mL) at −78° C., n-BuLi in hexanes (1.6 M; 18.2 mL, 29.0 mmol) was slowly added through a dripping funnel. When the addition was complete, the mixture was kept at −78° C. for 1 h. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.11 mL, 34.8 mmol) was then added in one portion. The mixture was allowed to warm up room temperature and stirred for 1 h, then the reaction was quenched with water and the solution was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give the sub-title compound as a colorless oil. LCMS calc. for C15H21BF2O3Na (M+Na)+ m/z=321.2. found: 321.0.

後処理

  1. additionWhen the addition
  2. customthe reaction was quenched with water
  3. extractionthe solution was extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-facb8638362c450f96cd170bf626bcd3
出典データセット
uspto-grants-2015_12
特許番号
US09200004B2

反応ノート

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