Sodium hydride → HCID 68135265, compound

HRID 1288082Notes

Reaction equation

HRID 1288082 reaction equation
[O:1]=[C:2]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:3]P(=O)(OC)OC.[H-].[Na+].[CH3:17][O:18][C:19](=[O:38])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[C:30](=[O:31])[CH2:29][CH:28]([O:32][C:33](=[O:35])[CH3:34])[CH:27]1[CH:36]=O>O1CCCC1>[CH3:17][O:18][C:19](=[O:38])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[C:30](=[O:31])[CH2:29][CH:28]([O:32][C:33](=[O:35])[CH3:34])[CH:27]1[CH:36]=[CH:3][C:2](=[O:1])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 580181Dimethyl (2-oxoheptyl)phosphonateHCID 54566940HCID 54566940, compound

Product 1

HCID 68135265HCID 68135265, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

70 Mg. of dimethyl 2-oxoheptylphosphonate in 2 ml. of tetrahydrofuran is added to 12 mg. of 48% sodium hydride in 1 ml. of tetrahydrofuran, and the mixture stirred at 0°C. under nitrogen for 30 minutes. 70 Mg. of 3-acetoxy-2-formyl-5-oxocyclopentaneheptanoic acid methyl ester, 5-cyclic ethylene ketal in 2 ml. of tetrahydrofuran is then added dropwise and the mixture allowed to warm to 20°-25°C. After 3 hours the mixture is chilled, added to cold saturated aqueous NaH2PO4, extracted with ethyl acetate, and the latter extract dried over Na2SO4 and concentrated to dryness. The residue is purified by silica gel chromatography (7.8 g. silica gel), eluting with 7% acetone in chloroform to give 3-acetoxy-2-(3-oxo-1-octenyl)-5-oxocyclopentaneheptanoic acid methyl ester, 5-cyclic ethylene acetal: ir (CHCl3) 5.78, 5.9, 6.0, 6.17, 8.00, 10.55 μ; U.V. λmaxCH3OH 228 mμ (Em 10,050).

Workup

  1. temperatureto warm to 20°-25°C
  2. temperatureAfter 3 hours the mixture is chilled
  3. extractionextracted with ethyl acetate
  4. extractionthe latter extract
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by silica gel chromatography (7.8 g. silica gel)
  8. washeluting with 7% acetone in chloroform

Sources & evidence

ORD record
ord-6eda16a5adbf4b35a14e5553eff52c49
Source dataset
uspto-grants-1976_10
Patent number
US03987082

Reaction notes

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