Hexane → 2-(4-Bromophenyl)propane-1,3-diol

HRID 515457

반응식

HRID 515457 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:14][OH:15])[CH2:9][OH:10])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8058HexaneHCID 9855836Potassium sodium tartarateHCID 10519382Diethyl 4-bromophenylmalonateHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 218667012-(4-Bromophenyl)propane-1,3-diol수율 37.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

To a solution of diethyl 2-(4-bromophenyl)malonate (18.1 g, 57.5 mmol) in ether (285 ml) was added 0.98M-diisobutylaluminium hydride in hexane (259 ml, 254 mmol) at 0° C. under nitrogen atmosphere. The resulting mixture was stirred at 0° C. for 4 hours. Aqueous potassium sodium tartrate (0.57M, 500 ml) was added to the reaction mixture for quenching the aluminum reagent and the mixture was stirred for 14 hours. The organic layer was extracted with ethyl acetate and dried over sodium sulfate. After concentration, the residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=40/60 to ethyl acetate only) to afford 2-(4-bromophenyl)propane-1,3-diol as white solid (4.97 g, 37%).

후처리

  1. customfor quenching the aluminum reagent
  2. stirringthe mixture was stirred for 14 hours
  3. extractionThe organic layer was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration
  6. customthe residue was purified by silica gel column chromatography (eluant

출처 및 근거

ORD 기록
ord-073ca934b9104bed9e97062c70542276
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108957B2

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