Triethylamine → HCID 53958373, compound

HRID 1461143Notes

Reaction equation

HRID 1461143 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:36])[CH:10]([CH3:35])[CH2:11][C:12]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:13](O)[CH2:14][CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(Cl)(Cl)(Cl)Cl.CC(C)=O.C(=O)=O.FC(F)(F)S(Cl)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:23]1([C:12]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH2:11][CH:10]([N:9]([CH3:36])[CH3:8])[CH3:35])[CH:13]=[CH:14][CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 53708236HCID 53708236, compoundHCID 86745300HCID 86745300, compound

Product 1

HCID 53958373HCID 53958373, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (2.49 ml, 17.88 mmol) was added to a stirred solution of ethyl 8-dimethylamino-6,6-diphenyl-5-hydroxynon-2-enoate (1.77 g, 4.47 mmol) in CH2Cl2 (30 ml) at -30° C. (CCl4 /acetone/CO2), and the solution was stirred for 5 min. Trifluoromethanesulfonyl chloride (0.38 ml, 4.91 mmol) was then added dropwise. The reaction mixture was stirred 15 min at -30° C., warmed to room temperature over 1 hour, and then stirred at room temperature for 2 hours. The mixture was diluted with CH2Cl2 (20 ml) and poured into 5% NaHCO3 (20 ml). The layers were separated, and the organic extracts were washed with brine (30 ml). The extracts were dried over Na2SO4 /trace K2CO3, filtered, and concentrated in vacuo on a rotary evaporator. The oily brown residue was applied to a column as described above, and eluted with 6% methanol in CHCl3 to yield 1.05 g of ethyl 6,6-diphenyl-8-dimethylaminonona-2,4-dienoate, as a clear light brown mobile oil.

Workup

  1. stirringThe reaction mixture was stirred 15 min at -30° C.
  2. stirringstirred at room temperature for 2 hours
  3. customThe layers were separated
  4. washthe organic extracts were washed with brine (30 ml)
  5. dry with materialThe extracts were dried over Na2SO4 /
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo on a rotary evaporator
  8. washeluted with 6% methanol in CHCl3

Sources & evidence

ORD record
ord-c27a7015e19a4edca69ebf8abb33df5e
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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