Hexane → Ethyl 5-phenylpent-2-enoate

HRID 1828119노트

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HRID 1828119 반응식
[CH2:1]1CCC(N=C=NC2CCCCC2)C[CH2:2]1.[C:16]1([CH2:22][CH2:23][CH:24]=[CH:25][C:26]([OH:28])=[O:27])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCCCCC>CN(C1C=CN=CC=1)C.CCO.C1COCC1>[CH2:1]([O:27][C:26](=[O:28])[CH:25]=[CH:24][CH2:23][CH2:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2]

참가 물질

7

반응물 3

HCID 8058HexaneHCID 10868DicyclohexylcarbodiimideHCID 5569995-phenylpent-2-enoic acid

생성물 1

HCID 562556Ethyl 5-phenylpent-2-enoate수율 61%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

The reagents DCC (33 mM) and DMAP (30 mM) were added to a solution of 5-phenylpent-2-enoic acid (5.3 g, 30 mM) in EtOH (50 mL) and THF (20 mL), which was cooled to 0° C. The resulting mixture was stirred for 30 min at 0° C., then allowed to react for 15 h at room temperature. The suspension was filtered, and the filtrate was concentrated. The residue was dissolved in EtOAc and washed with 1 M HCl (3×30 mL), H2O (10 mL), saturated NaHCO3 (3×30 mL), H2O (10 mL), saturated NaCl (20 mL), dried over MgSO4, and concentrated. Chromatography on a silica gel column using 1:2 EtOAc:hexane as the eluent afforded 5-phenyl-pent-2-enoic acid ethyl ester (3.75 g, yield=61%).

후처리

  1. customto react for 15 h at room temperature
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 1 M HCl (3×30 mL), H2O (10 mL), saturated NaHCO3 (3×30 mL), H2O (10 mL), saturated NaCl (20 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8beb8a76caed4413b209fbbfcb6cd652
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07056947B2

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