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

HRID 1182510ノート

反応式

HRID 1182510 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-c468b8de8008435a92738b2568b41e83
出典データセット
uspto-grants-2007_10
特許番号
US07288567B2

反応ノート

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