Ethylene Glycol → HCID 54367906, compound

HRID 1196260Notes

Reaction equation

HRID 1196260 reaction equation
[N+:1]([CH2:4][CH:5]1[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][C:7](=O)[CH2:6]1)([O-:3])=[O:2].[CH2:24]([OH:27])[CH2:25][OH:26].Cl[Si](C)(C)C>C(Cl)Cl>[N+:1]([CH2:4][CH:5]1[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][C:6]21[O:27][CH2:24][CH2:25][O:26]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 54034481HCID 54034481, compound

Product 1

HCID 54367906HCID 54367906, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-nitromethyl-4,4-diphenylcyclohexanone (69 g), ethylene glycol (30.48 g) and chlorotrimethylsilane (106.8 g) in anhydrous methylene chloride (1 liter) is brought to reflux for 2 hours, then cooled to +25° C., washed with saturated aqueous sodium hydrogen carbonate solution (600 cc) and then with saturated aqueous sodium chloride solution (300 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel with a slight excess pressure of nitrogen (0.04-0.063 mm, diameter 6.5 cm, height 45 cm), eluting with a mixture of cyclohexane and ethyl acetate (90:10 by volume) and collecting 500-cc fractions. Fractions 1 to 3 are combined and concentrated to dryness under reduced pressure (2.7 kPa). (RS)-6-Nitromethyl-7,7-diphenyl-1,4-dioxaspiro[4.5]decane (63.3 g) is obtained in the form of white crystals, m.p. 148° C.

Workup

  1. temperatureto reflux for 2 hours
  2. temperaturecooled to +25° C.
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution (600 cc)
  4. dry with materialwith saturated aqueous sodium chloride solution (300 cc), dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is chromatographed on a column of silica gel with a slight excess pressure of nitrogen (0.04-0.063 mm, diameter 6.5 cm, height 45 cm)
  8. washeluting with a mixture of cyclohexane and ethyl acetate (90:10 by volume)
  9. customcollecting 500-cc fractions
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-cd4372ef09da46229f35cbed415a7658
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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