1,3-Dibromopropane → HCID 92135508、化合物

HRID 925120

反応式

HRID 925120 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:23][CH2:24][CH2:25]Br>ClCCl.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:16]#[N:17])[CH2:25][CH2:24][CH2:23]2)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 2979634-Benzyloxy-3-methoxyphenylacetonitrile

生成物 1

HCID 92135508HCID 92135508、化合物収率 50.1%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile (3.1 g, 12.24 mmol) in dichloromethane (30 mL) was added sodium hydroxide (30 mL, 50% aqueous solution, 367 mmol), TBAB (0.99 g, 3.06 mmol) and then with 1,3-dibromopropane (2 mL, 19.58 mmol). The reaction was stirred at room temperature for 72 hours. The layers were separated, organic layer was dried (MgSO4) and concentrated. Purification by flash chromatography (silica gel, 5-25% EtOAc/hexane) afforded 1-(4-(benzyloxy)-3-methoxyphenyl)cyclobutanecarbonitrile (1.8 g, 50%). MS (ESI) m/z 294 (M+H)+.

後処理

  1. customThe layers were separated
  2. dry with materialorganic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by flash chromatography (silica gel, 5-25% EtOAc/hexane)

出典と根拠

ORDレコード
ord-4ba382dbcae64e058b3315ac9ebb5dd1
出典データセット
uspto-grants-2016_03
特許番号
US09284272B2

関連ノート

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