Ethyl Acetate → (6-methoxy-2,3-dihydro-1H-inden-5-yl)boronic acid

HRID 985563ノート

反応式

HRID 985563 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[CH2:7][CH2:6][CH2:5]2.[Li]CCCC.[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C.CCOC(C)=O>C1COCC1>[CH3:12][O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][CH2:7]2)=[CH:3][C:2]=1[B:18]([OH:23])[OH:19]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 21531Triisopropyl borateHCID 152482825-bromo-6-methoxy-2,3-dihydro-1H-indeneHCID 178418339Butyllithium

生成物 1

HCID 22278823(6-methoxy-2,3-dihydro-1H-inden-5-yl)boronic acid収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 1.06 g (4.69 mmol) of 5-bromo-6-methoxyindane in 10 mL of THF was cooled to −78° C. and treated in a dropwise manner with 2.90 mL (4.64 mmol) of 1.6 M n-BuLi in hexanes. The mixture was stirred for 1 hr and was treated with 1.90 mL (8.2 mmol) of triisopropyl borate. The reaction was allowed to warm slowly to 0° C. and was stirred at this temperature for 0.5 hr. The reaction was quenched by the careful addition of 12 mL of aq 1N HCl. The layers were separated and the aqueous layer extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford 1.02 g. Flash chromatography (SiO2; 15% EtOAc in hexanes) gave 0.62 g (69%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.52 (s, 2H), 7.41 (s, 1H), 6.84 (s, 1H), 3.75 (s, 3H), 2.81 (t, J=7.3 Hz, 2H), 2.73 (t, J=7.3 Hz, 2H), 2.00-1.92 (m, 2H); IR (CHCl3) 3505 (br), 2945, 1612, 1570, 1487, 1465, 1417, 1297, 1252, 1161, 1129 cm−1; FDMS 192 (M+).

後処理

  1. stirringwas stirred at this temperature for 0.5 hr
  2. customThe reaction was quenched by the careful addition of 12 mL of aq 1N HCl
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (3×50 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford 1.02 g

出典と根拠

ORDレコード
ord-682f831641f940be864443ccbfc2bf10
出典データセット
uspto-grants-2005_03
特許番号
US06872743B2

反応ノート

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