HCID 15234843, compound → HCID 77768440, compound

HRID 1757219Notes

Reaction equation

HRID 1757219 reaction equation
[O:1]=[C:2]1[CH:6]=[C:5]([CH2:7]P(=O)(OC)OC)[CH2:4][O:3]1.[N:14]1([CH2:19][CH2:20][O:21][CH:22]2[CH2:34][CH2:33][C:25]3([CH2:30][CH2:29][CH:28]([CH:31]=O)[CH2:27][CH2:26]3)[CH2:24][CH2:23]2)[CH2:18][CH2:17][CH2:16][CH2:15]1>O1CCCC1.[H-].[Na+]>[N:14]1([CH2:19][CH2:20][O:21][CH:22]2[CH2:34][CH2:33][C:25]3([CH2:30][CH2:29][CH:28]([CH:31]=[CH:7][C:5]4[CH2:4][O:3][C:2](=[O:1])[CH:6]=4)[CH2:27][CH2:26]3)[CH2:24][CH2:23]2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 15234843HCID 15234843, compoundHCID 15234844HCID 15234844, compound

Product 1

HCID 77768440HCID 77768440, compoundYield 108%

Reagents, catalysts & solvents 2

HCID 24758Sodium hydrideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.045 mg, 60% dispersion in mineral oil) was added under nitrogen atmosphere and at room temperature, to a mixture of 0.740 g of dimethyl (2-oxo-[5H]-4-furyl)methylphosphonate and 0.080 g of 9-(2-(N-pyrrolidinyl)ethoxy)-3-formyl-spiro[5.5]-undecane (I-af, Ex. 30) in 5 ml of anhydrous tetrahydrofuran. After 2 hrs the reaction was quenched with sodium dihydrogenophosphate (5% water solution) and diluted with ethyl acetate; the organic layer was separated, dried over sodium sulfate and evaporated to dryness under reduced pressure The residue was purified by flash chromatography (SiO2 ; chloroform/methanol 80/20) to give 0.110 g of (EZ)-9-(2-(N-pyrrolidinyl)ethoxy)-3-(2-(2-oxo-[5H]-4-furyl)vinyl)-spiro[5.5]-undecane (I-b) as amorphous solid. TLC: Rf=0.32 (SiO2 plates, chloroform/methanol 80/20). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 6.50-5.70 (2H, m); 6.30 (1H, bs); 4.81 (2H, bs); 3.68 (2H, t), 3.45(1H, m), 2.75 (2H, t), 2.70-2.00 (5H, m); 1.97-0.99 (22H, m).

Workup

  1. customAfter 2 hrs the reaction was quenched with sodium dihydrogenophosphate (5% water solution)
  2. additiondiluted with ethyl acetate
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness under reduced pressure The residue
  6. customwas purified by flash chromatography (SiO2 ; chloroform/methanol 80/20)

Sources & evidence

ORD record
ord-8f267fcf7bfc4597990bf0fc1b9daf82
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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