Phenethyl bromide → HCID 22618832、化合物

HRID 635480ノート

反応式

HRID 635480 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][C:11](=[O:22])[CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([CH2:29][CH2:30][Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(CCBr)C=CC=CC=1.[Mg].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH2:30][CH2:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([OH:22])[CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 7666Phenethyl bromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 226187871,5-Dibenzyloxy-3-pentanoneHCID 178419670HCID 178419670、化合物

生成物 1

HCID 22618832HCID 22618832、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 1,5-dibenzyloxy-3-pentanone (13.9 g) in tetrahydrofuran (150 ml) was dropwise added a solution of 2-phenylethyl-magnesium bromide, which was prepared from 2-phenylethyl bromide (24 g) and magnesium (3.1 g), in tetrahydrofuran (100 ml) under ice-cooling. The mixture was stirred under ice-cooling for 90 minutes, poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue obtained was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1) to give the subject compound (8.1 g) as a colorless oily substance.

後処理

  1. temperaturecooling
  2. temperaturecooling for 90 minutes
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  5. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-b020010bbda0458ab007c5cab772613e
出典データセット
uspto-grants-2001_02
特許番号
US06187821B1

反応ノート

読み込み中…