Triethylamine → 6-[4-(1-Phenylethenyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

HRID 611370Notes

Reaction equation

HRID 611370 reaction equation
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[C:11]1([C:17]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)=[CH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O.O>[C:11]1([C:17]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([N:8]3[CH2:9][CH2:10][C:5]4[CH:4]=[CH:3][O:2][C:6]=4[CH2:7]3)=[O:24])=[CH:26][CH:27]=2)=[CH2:18])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochlorideHCID 195999084-(1-Phenylethenyl)benzoic acid

Product 1

HCID 196001706-[4-(1-Phenylethenyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.527 g (3.302 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.74 g (3.30 mmol) of 4-(1-phenylethenyl)benzoic acid and 1.84 ml (13.2 mmol) of triethylamine in 15 ml of N,N-dimethylformamide, 0.60 ml (3.96 mmol) of diethyl cyanophosphonate was added dropwise, followed by overnight stirring at room temperature. This mixture was poured into water and extracted with diethyl ether 3 times. The combined organic layer was dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1) to yield 6-[4-(1-phenylethenyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine.

Workup

  1. extractionextracted with diethyl ether 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1)

Sources & evidence

ORD record
ord-46e9ecbbf5de4c7a8b647883fb8158e6
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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