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

HRID 7734

反応式

HRID 7734 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

[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)+.

後処理

  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

出典と根拠

ORDレコード
ord-34ed716cd4364862b6fb3902c6311fb6
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

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