Phenethyl bromide → HCID 22618832, 화합물

HRID 842285노트

반응식

HRID 842285 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-41cd1f52b8d949699a0c314ddbdab2fa
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372800B1

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