2-(4'-Benzyloxybutyl)-2-methyloxepane-6-ol → 2-(4'-Benzyloxybutyl)-2-methyl-oxepan-6-one

HRID 851331Notes

Reaction equation

HRID 851331 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1([CH3:21])[CH2:19][CH2:18][CH2:17][CH:16]([OH:20])[CH2:15][O:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.N1C=CC=CC=1.[O-2].[O-2].[O-2].[Cr+6]>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1([CH3:21])[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[CH2:15][O:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 131881822-(4'-Benzyloxybutyl)-2-methyloxepane-6-ol

Product 1

HCID 131881832-(4'-Benzyloxybutyl)-2-methyl-oxepan-6-oneYield 101.6%

Reagents, catalysts & solvents 2

HCID 131712986HCID 131712986, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Dry celite (50 g) and 2-(4'-benzyloxybutyl)-2-methyloxepane-6-ol (6.9 g, 0.02 mol) in methylene chloride are added to a pyridine-chromium trioxide solution [prepared from pyridine (22.4 g, 0.284 mol) and chouromium trioxide (14.2 g, 0.142 mol)] in dry methylene chloride (800 ml) at 10° C. in a nitrogen atmosphere. After 2 hours of stirring the mixture is filtered and the celite cake is washed with methylene chloride (10×50 ml). The solvent is removed at reduced pressure. The residue is diluted with ether (200 ml), filtered and the solvent is removed at reduced pressure. The crude product is chromatographed on SilicAR CC-7 (150 g) in hexane. Elution with 10% ethyl acetate/hexane gives 2-(4'-benzyloxybutyl)-2-methyl-oxepan-6-one (11) as a clear colorless oil (5.9 g, 86%).

Workup

  1. filtrationis filtered
  2. washthe celite cake is washed with methylene chloride (10×50 ml)
  3. customThe solvent is removed at reduced pressure
  4. additionThe residue is diluted with ether (200 ml)
  5. filtrationfiltered
  6. customthe solvent is removed at reduced pressure
  7. customThe crude product is chromatographed on SilicAR CC-7 (150 g) in hexane
  8. washElution with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-08f2da7ef41e49f2beb954893a6c2583
Source dataset
uspto-grants-1983_05
Patent number
US04384126

Reaction notes

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