1,4-Dibromobutane → 1-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile

HRID 7734

반응식

HRID 7734 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[C:12]([O:19][CH3:20])[CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:32][CH2:33][CH2:34][CH2:35]Br>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:17]#[N:18])[CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:12]([O:19][CH3:20])[CH:11]=1

참가 물질

5

반응물 3

HCID 80561,4-DibromobutaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10192854Boma

생성물 1

HCID 102366671-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile (130 mg, 0.49 mmol) in THF (5.0 mL) was cooled to −78° C. under argon atmosphere. Sodium bis(trimethylsilyl)amide (1.8 mL, 1.08 mmol) was added slowly and after fifteen minutes, added 1,4-dibromobutane (0.07 mL, 0.59 mmol) to dark brown reaction mixture. Let mixture warm to rt overnight. After concentrating reaction mixture in vacuo, the resulting pink oil was purified by flash chromatography, using a gradient elution of 1:9 EtOAc:hexanes to 1:4 EtOAc:hexanes. This afforded the desired compound, 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile, as a yellow solid. 1H NMR(CDCl3, 300 MHz) δ 7.86–7.26 (m, 7H), 4.07 (s, 3H), 2.59–1.91 (m, 8H). MS (ESI) 319.1 (M+H)+.

후처리

  1. concentrationAfter concentrating
  2. customreaction mixture in vacuo
  3. customthe resulting pink oil was purified by flash chromatography
  4. washa gradient elution of 1:9 EtOAc

출처 및 근거

ORD 기록
ord-34ed716cd4364862b6fb3902c6311fb6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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