Triethylamine → HCID 54510614, compound

HRID 325548Notes

Reaction equation

HRID 325548 reaction equation
O[CH2:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:23]([C:37]([O:39][CH3:40])=[O:38])[CH2:24][CH:25]=[CH:26][CH2:27]CCCCCCCCC.[CH3:41]S(Cl)(=O)=O.C([N:48]([CH2:51][CH3:52])CC)C>CCOCC>[CH2:2]([NH:48][C:51]1[CH:52]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:23][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21226445Aluminium lithium hydrideHCID 53905731Pentadec-4-en-1-olHCID 54174139HCID 54174139, compound

Product 1

HCID 54510614HCID 54510614, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a cold (-20°) stirred solution of 10.8 g. 1-hydroxypentadec-4-ene prepared by lithium aluminum hydride reduction of methyl tetradec-3-encarboxylate and 13.4 ml. triethylamine in 300 ml. ether is added dropwise 5.6 ml. methanesulfonyl chloride in 5 ml. of either. After addition is completed, the solution is warmed to room temperature, stirred for 30 minutes and filtered directly into a solution of 23.1 g. ethyl 2-aminophenyl acetate in 100 ml. ether. After 17 hours at room temperature, the precipitate is filtered and washed with several portions of methylene chloride. The organic solution is washed twice with 100 ml. water, 100 ml. brine, dried and evaporated. The tan residue is crystallized from ethanol and from acetonitrile to yield the title compound as white crystals.

Workup

  1. additionAfter addition
  2. stirringstirred for 30 minutes
  3. filtrationfiltered directly into a solution of 23.1 g
  4. filtrationthe precipitate is filtered
  5. washwashed with several portions of methylene chloride
  6. washThe organic solution is washed twice with 100 ml
  7. dry with materialbrine, dried
  8. customevaporated
  9. customThe tan residue is crystallized from ethanol and from acetonitrile

Sources & evidence

ORD record
ord-e4775e79dfab43979af0a82f0581fa95
Source dataset
uspto-grants-1984_04
Patent number
US04440940

Reaction notes

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