Benzyl Alcohol → 3-(5-Benzyloxypentyl)-7,7-ethylenedioxy-3-hydroxy-cis-bicyclo[3,3,0]octane

HRID 2395819Notes

Reaction equation

HRID 2395819 reaction equation
[CH2:1]1[CH2:13][O:12][C:3]2([CH2:10][C@@H:9]3[C@@H:5]([CH2:6][C:7](=[O:11])[CH2:8]3)[CH2:4]2)[O:2]1.[CH2:14]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Mg].C(Br)CCCCBr.C(O)C1C=CC=CC=1.[Cl-].[NH4+]>C(OCC)C>[CH2:14]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:7]1([OH:11])[CH2:6][C@@H:5]2[C@@H:9]([CH2:10][C:3]3([O:2][CH2:1][CH2:13][O:12]3)[CH2:4]2)[CH2:8]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 6

HCID 244Benzyl AlcoholHCID 81001,5-DibromopentaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11030443(3'aR,6'aS)-hexahydro-1'H-spiro(1,3-dioxolane-2,2'-pentalen)-5'-oneHCID 14221121Benzyl 5-Bromoamyl Ether2×

Product 1

HCID 228526723-(5-Benzyloxypentyl)-7,7-ethylenedioxy-3-hydroxy-cis-bicyclo[3,3,0]octaneYield 56.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 501 mg of 7,7-ethylenedioxy-3-oxo-cis-bicyclo[3,3,0]octane in 5 ml of diethyl ether was added dropwise at room temperature to 5-benzyloxy-pentamethylene-magnesium bromide, which had been prepared in 5 ml of diethyl ether from 1.00 g of 5-benzyloxypentyl bromide and 100 mg of metallic magnesium at room temperature. The 5-benzyloxypentyl bromide, in turn, had been prepared from pentamethylene bromide and benzyl alcohol according to the method of A. W. Burgstabler et al. [J. Org. Chem. 42, 566 (1977)]. The mixture was stirred for 1.5 hours at room temperature. Upon completion of the reaction, an aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, giving 1.47 of residue. On purifying the residues by silica gel column chromatography, 556 mg of the title compound were obtained as an oil from the fractions eluted with hexane containing 25-30% by volume of ethyl acetate.

Workup

  1. customUpon completion of the reaction
  2. extractionwas then extracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customgiving 1.47 of residue
  7. customOn purifying the residues by silica gel column chromatography

Sources & evidence

ORD record
ord-1b4d317dc43c4cb89a8f2a22735d6572
Source dataset
uspto-grants-1996_02
Patent number
US05489613

Reaction notes

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