Ethanol → HCID 53824747, compound

HRID 2291638Notes

Reaction equation

HRID 2291638 reaction equation
[Na].[C:2]([O:9]C)(=O)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Si:11]([O:28][CH2:29][CH2:30][CH2:31][CH:32]1[O:34][CH:33]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:41](O)C>>[Si:11]([O:28][CH2:29][CH2:30][CH2:31][C@H:32]1[O:34][C:2](=[O:9])[CH:3]([C:4]([O:6][CH2:7][CH3:41])=[O:5])[C@@H:33]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 7943Dimethyl malonateHCID 5360545SodiumHCID 86742666HCID 86742666, compound

Product 1

HCID 53824747HCID 53824747, compound

Procedure

Sodium (0.64 g) was added to ethanol (30 ml) at ambient temperature, followed by dimethyl malonate (3.2 ml), and the resulting mixture was stirred at ambient temperature for 15 minutes. A solution of (2R*, 3R*)-3-[3-(t-butyldiphenylsilyloxy)propyl]-2phenyloxirane (2.90 g) in ethanol (30 ml) was added thereto. After being refluxed for 12 hours, the reaction mixture was evaporated in vacuo and the residue was dissolved in ethyl acetate. The organic solution was washed with lN hydrochloric acid, water and brine successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (150 g) eluting with a mixture of hexane and ethyl acetate (50:1 to 10:1) to give ethyl (4R*,5R*)5-[3-(t-butyldiphenylsilyloxy)propyl]-2-oxo-4-phenyltetrahydro-3-furancarboxylate (2.64 g).

Workup

  1. temperatureAfter being refluxed for 12 hours
  2. customthe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic solution was washed with lN hydrochloric acid, water and brine successively
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel (150 g)
  8. washeluting with a mixture of hexane and ethyl acetate (50:1 to 10:1)

Sources & evidence

ORD record
ord-d1c662baaf384c00a881ba98a4baac49
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

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