Water → HCID 57306106, compound

HRID 2399337Notes

Reaction equation

HRID 2399337 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[C:18]([C:24]([O:26]C)=[O:25])[CH2:19][C:20]([O:22]C)=[O:21].C[N+]1([O-])CC[O:32]CC1.O.OS([O-])=O.[Na+]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O.CC(C)=O>[C:24]([C@:18]1([OH:32])[C@H:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[O:21][C:20](=[O:22])[CH2:19]1)([OH:26])=[O:25]

Participants

8

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 54320560HCID 54320560, compound

Product 1

HCID 57306106HCID 57306106, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of (E) methyl 12-(2,4-dichlorophenyl)-3-methoxycarbonyl-3-dodecenoate (1.50 g, 3.61 mmol), osmium tetroxide (0.229 ml of a 2% solution in t-butanol, 0.018 mmol), N-methylmorpholine-N-oxide (634 mg, 5.42 mmol), water (2 ml), and acetone (2 ml) was stirred at room temperature for 64 h. Aqueous NaHSO3 (1.1M, 6 ml) was added, and the mixture filtered, after 20 min, through a plug of silica gel. The silica gel plug was washed with ether, then the filtrate washed with aqueous HCl, water, and saturated aqueous NaCl. After drying (MgSO4), the solvent was removed under vacuum, and the residue purified by chromatography on silica gel (50-100% ether/petroleum ether 40°-60° C.) to give the title compound (1.33 g), contaminated with the 5-ring lactone.

Workup

  1. filtrationthe mixture filtered, after 20 min, through a plug of silica gel
  2. washThe silica gel plug was washed with ether
  3. washthe filtrate washed with aqueous HCl, water, and saturated aqueous NaCl
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent was removed under vacuum
  6. customthe residue purified by chromatography on silica gel (50-100% ether/petroleum ether 40°-60° C.)

Sources & evidence

ORD record
ord-69a261e81ac14989b820694a6e7da441
Source dataset
uspto-grants-1995_09
Patent number
US05447954

Reaction notes

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