Iodoethane → 2-Ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile

HRID 1853908

반응식

HRID 1853908 반응식
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].[CH2:21](I)[CH3:22].[CH2:24]1COC[CH2:25]1>CN(C=O)C>[CH2:24]([C:15]([C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:18])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)([CH2:21][CH3:22])[C:16]#[N:17])[CH3:25]

참가 물질

6

반응물 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 38429222-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile

생성물 1

HCID 682291472-Ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile수율 38%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (2.0 g, 8.23 mmol) in DMF (40 mL) was cooled to 0° C. and sodium hydride (60 wt %, 1.2 g, 32.9 mmol) added portion wise. The mixture was stirred for 10 min and ethyl iodide (0.74 mL, 9.05 mmol) in THF (10 mL) was added. The mixture was stirred at room temperature for 12 h. The reaction mixture was quenched with water and diluted with ethyl acetate. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (950 mg, 38%) as a brown solid: ESI MS m/z 300 [C18H26BNO2+H]+.

후처리

  1. stirringThe mixture was stirred at room temperature for 12 h
  2. customThe reaction mixture was quenched with water
  3. additiondiluted with ethyl acetate
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-23bd53f8e0c444068da1b35f3745bbb6
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962648B2

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