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

HRID 1182510Notes

Reaction equation

HRID 1182510 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-c468b8de8008435a92738b2568b41e83
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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