Diethyl Ether → HCID 15698114, compound

HRID 465812Notes

Reaction equation

HRID 465812 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH:9]([CH2:15][CH:16]=C)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:20].[Na+].CCOCC>[Os](=O)(=O)(=O)=O.O>[C:10]([CH:9]([C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:18])[CH2:15][CH:16]=[O:20])([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 15698113Ethyl 3-(4-methylphenyl)-3-oxo-2-(allyl)propanoateHCID 23667635Sodium periodate2×

Product 1

HCID 15698114HCID 15698114, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalyst3×HCID 962WaterSolvent

Procedure

Ethyl 3-(4-methylphenyl)-3-oxo-2-(allyl)-propanoate (74.21 g, 301 mmol, 1.0 eq), osmium tetroxide (100 mg, cat.), sodium metaperiodate (141.8 g, 663 mmol, 2.2 eq), ether (500 mL) and water (1 L) were mixed and stirred at room temperature. After 24 hours, an additional 110 mg of OsO4 was added and after another 24 hours, 200 mg more of OsO4 was added together with sodium metaperiodate (190 g, 888 mmol, 3.0 eq). After 4 days, the layers were separated and the ether layer washed with aqueous sodium bisulfite (1×500 mL) followed by brine (1×300 mL). The ether layer was dried (MgSO4) and the solvent removed in vacuo to yield 64.99 g of a dark brown oil. This oil was flash chromatographed over silica gel in 4:1 hexane/ethyl acetate to yield 37.5 g of an amber oil. NMR (200 MHz, CDCl3 ) δ9.79 (s, 1H); 7.93 (d, 2H, J=9 Hz); 7.27 (d, 2H, J=9 Hz); 4.87 (t, 1H, J=7 Hz); 4.13 (q, 2H, J=7 Hz); 3.37-3.08 (AB multiplet, 2H); 2.40 (s, 3H); 1.14 (t, 3H, J=7 Hz). Anal. Calcd. for C14H16O4 : C, 67.73; H, 6.50. Found: C, 67.53; H, 6.54.

Workup

  1. waitAfter 4 days
  2. customthe layers were separated
  3. washthe ether layer washed with aqueous sodium bisulfite (1×500 mL)
  4. dry with materialThe ether layer was dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-374423409cde43979293d4b4635b8797
Source dataset
uspto-grants-1992_10
Patent number
US05153197

Reaction notes

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