Tetrahydrofuran → (E,E)-Ethyl-7-[(4-biphenyl)carbonyl]-2,4-heptadienoate

HRID 1182510노트

반응식

HRID 1182510 반응식
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([C:7]([CH2:9][CH2:10][CH:11]=O)=[O:8])=[CH:3][CH:2]=1.C(C(P(O)(O)=O)/C(/CC)=[C:23](\[CH2:27][CH3:28])/[C:24]([O-:26])=[O:25])C.[H-].[Na+].[CH2:37]1COC[CH2:38]1>>[CH2:37]([O:26][C:24](=[O:25])/[CH:23]=[CH:27]/[CH:28]=[CH:11]/[CH2:10][CH2:9][C:7]([C:4]1[CH:5]=[CH:6][C:1]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:2][CH:3]=1)=[O:8])[CH3:38]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 235874133-[(4-Biphenyl)carbonyl]propionaldehydeHCID 86585716(E)-2,3-diethyl-4-phosphonohex-2-enoate

생성물 1

HCID 57780781(E,E)-Ethyl-7-[(4-biphenyl)carbonyl]-2,4-heptadienoate수율 40%

실험 절차

To a solution of aldehyde 201 (180 mg, 0.75 mmol) in THF (10 mL), stirred at 0° C. under nitrogen, was added triethyl-4-phosphonocrotonate (220 μL, 0.98 mmol) followed by sodium hydride (40 mg, 0.98 mmol). The mixture was allowed to warm up to room temperature in 2 hours and then quenched by adding water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated. Purification by flash silica gel chromatography (30% ethyl acetate in hexane) afforded the corresponding diene 202 (100 mg, 40% yield). MS (ESI)=335 (MH+).

후처리

  1. customquenched
  2. additionby adding water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-c468b8de8008435a92738b2568b41e83
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288567B2

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