Triethylamine → HCID 15606012, compound

HRID 1025685Notes

Reaction equation

HRID 1025685 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][C:2]1([CH2:9][CH2:10][OH:11])[CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[S:19](Cl)([CH3:22])(=[O:21])=[O:20]>C(Cl)Cl>[CH3:22][S:19]([O:11][CH2:10][CH2:9][C:2]1([CH2:6][CH2:7][O:8][S:19]([CH3:22])(=[O:21])=[O:20])[O:3][CH2:4][CH2:5][O:1]1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5760201,3-Dioxolane-2,2-diethanol

Product 1

HCID 15606012HCID 15606012, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 2,2′-(1,3-dioxolane-2,2-diyl)diethanol (1.3 g, 8.0 mmol) in methylene chloride (100 mL) was added triethylamine (3.4 mL, 24 mmol) at room temperature. The solution was cooled down to −40° C. and then mesyl chloride (1.65 mL, 20 mmol) was added dropwise. The reaction mixture was stirred at −40° C. for 30 min, then warmed up to 0° C. gradually. The reaction was quenched with saturated aqueous NaHCO3 solution. The aqueous layer was extracted with methylene chloride. The combined organic extracts were washed with brine, dried over Na2SO4, then evaporated to afford the crude product, 1,3-dioxolane-2,2-diyldiethane-2,1-diyl dimethanesulfonate: MS (m/e): 319 (M−1-1)+.

Workup

  1. temperaturewarmed up to 0° C. gradually
  2. customThe reaction was quenched with saturated aqueous NaHCO3 solution
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-5b39ee2093744340af594a967838d94f
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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