Triethylamine → HCID 67586603, compound

HRID 611312Notes

Reaction equation

HRID 611312 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.[Cl:11][C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]\[C:20]2[CH:25]=[CH:24][C:23]([C:26](O)=[O:27])=[CH:22][CH:21]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O.O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15](/[CH:18]=[CH:19]\[C:20]2[CH:21]=[CH:22][C:23]([C:26]([N:8]3[CH2:9][CH2:10][C:5]4[CH:4]=[CH:3][O:2][C:6]=4[CH2:7]3)=[O:27])=[CH:24][CH:25]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochlorideHCID 69554542HCID 69554542, compound

Product 1

HCID 67586603HCID 67586603, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.173 g (7.349 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 1.90 g (7.35 mmol) of (Z)-4-chloro-4'-stilbenecarboxylic acid and 4.10 ml (29.4 mmol) of triethylamine in 30 ml of N,N-dimethylformamide, 1.34 ml (8.82 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 the desired product.

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-5bd8be580f5e467b8791845758cb80dd
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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