Triethylamine → 3-Ethyl-5-((methylsulfonyl)oxy)-3-(3-nitrophenyl)pentyl methanesulfonate

HRID 397749Notes

Reaction equation

HRID 397749 reaction equation
[CH2:1]([C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)([CH2:7][CH2:8][OH:9])[CH2:4][CH2:5][OH:6])[CH3:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C1(C)C=CC=CC=1>[CH3:26][S:27]([O:6][CH2:5][CH2:4][C:3]([CH2:1][CH3:2])([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[CH2:7][CH2:8][O:9][S:27]([CH3:26])(=[O:29])=[O:28])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 230010213-Ethyl-3-(3-nitrophenyl)-1,5-pentanediol

Product 1

HCID 230010093-Ethyl-5-((methylsulfonyl)oxy)-3-(3-nitrophenyl)pentyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-ethyl-3-(3-nitrophenyl)-1,5-pentanediol (Preparation 61, 661 mg, 2.27 mmol) in toluene (24 ml) was added triethylamine (0.76 ml, 5.43 mmol) followed by methanesulfonyl chloride (0.42 ml, 5.4 mmol). The reaction mixture was stirred at room temperature under nitrogen for 18 h. The reaction mixture was poured onto water (10 ml), the phases were separated and the aqueous layer was extracted with dichloromethane (10 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an oil which was used without further purification (850 mg, 81% crude yield).

Workup

  1. additionThe reaction mixture was poured onto water (10 ml)
  2. customthe phases were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (10 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c0a80cc15134d27997375b5098ebf9b
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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