Triethylamine → HCID 67284191, compound

HRID 407865Notes

Reaction equation

HRID 407865 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH2:7]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH2:16][CH3:17])[C:10]=1[CH:18]1[C:26](=[O:27])[CH:25]2[CH:20]([CH:21]3[O:28][CH:24]2[CH2:23][CH2:22]3)[C:19]1=[O:29])[CH3:8].C(N(CC)CC)C>ClCCl>[CH2:5]([O:4][C:2](=[O:3])[O:29][C:19]1[CH:20]2[CH:25]([C:26](=[O:27])[C:18]=1[C:10]1[C:11]([CH2:16][CH3:17])=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=1[CH2:7][CH3:8])[CH:24]1[O:28][CH:21]2[CH2:22][CH2:23]1)[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 67284420HCID 67284420, compound

Product 1

HCID 67284191HCID 67284191, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of ethyl chloroformate (0.071 g, 0.65 mmol) in dichloromethane (0.5 ml) is added dropwise to a solution of (1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione (0.172 g, 0.55 mmol) in dichloromethane (2 ml) at 0° C. and the reaction mixture is stirred. A solution of triethylamine (0.066 g, 0.65 mmol) in dichloromethane (1 ml) is added and the reaction mixture is stirred at room temperature for 17 hours, warming slowly to room temperature. The reaction mixture is diluted with dichloromethane (3 ml) and washed with saturated aqueous sodium bicarbonate solution. The organic phase is separated, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give carbonic acid (1RS, 2SR,6RS,7SR)-5-oxo-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo-[5.2.1.02,6]-dec-3-en-3-yl ester ethyl ester as a colourless solid.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 17 hours
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. customThe organic phase is separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-509a3094802e47e2818ee2022b846419
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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