Phenethyl bromide → HCID 22618832, 화합물

HRID 617602노트

반응식

HRID 617602 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 22618832HCID 22618832, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-611d178e72ac47b991f2320e737c7b73
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05948820

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