Diiodomethane → 1-[2-(Cyclopropylmethoxy)ethyl]-4-(phenylmethoxy)benzene

HRID 1745866ノート

反応式

HRID 1745866 の反応式
[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH:2]=[CH2:3].I[CH2:22]I.[Cl-].[NH4+]>CCCCCC.C([Zn]CC)C>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][O:4][CH2:1][CH:2]2[CH2:22][CH2:3]2)=[CH:8][CH:9]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 22227278HCID 22227278、化合物

生成物 1

HCID 115146971-[2-(Cyclopropylmethoxy)ethyl]-4-(phenylmethoxy)benzene

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 178418750HCID 178418750、化合物溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of compound of formula (7), (12 g, 0.0447 mol) in dry hexane (50 ml), diethyl zinc (1.1 M solution in hexane, 185 ml) was added at 0° C. under nitrogen atmosphere followed by diiodomethane (18 ml, 0.224 mol). The reaction was stirred for 6 h at 0° C. and poured over cold aqueous solution of ammonium chloride. The organic layer was separated and the aqueous layer extracted repeatedly with diethyl ether. The combined organic layer was washed with aq. solution of sodium thiosulphate, dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified over silica gel column using ethyl acetate and light petroleum ether (1:50) as an eluent to afford compound of formula (8), as a colorless liquid 11.365 g (90%).

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted repeatedly with diethyl ether
  3. washThe combined organic layer was washed with aq. solution of sodium thiosulphate
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified over silica gel column

出典と根拠

ORDレコード
ord-5954218747e140378d0ce94f946ceb2b
出典データセット
uspto-grants-2006_03
特許番号
US07019172B2

反応ノート

読み込み中…