Acetonitrile → HCID 59058540, compound

HRID 2121279Notes

Reaction equation

HRID 2121279 reaction equation
[C:1]1([C:7]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10]S(=O)O2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O)(=O)=O.[C:33](#[N:35])[CH3:34]>>[CH3:34][C:33]1[O:10][C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:35]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 62406Trifluoromethanesulfonic acidHCID 59058541HCID 59058541, compound

Product 1

HCID 59058540HCID 59058540, compoundYield 64%

Conditions

Temperature
0 °C

Procedure

19 g (56.5 mmol) of (5R)-4,4,5-triphenyl-1,3,2-dioxathiolane 2-oxide in 90 ml of acetonitrile were introduced into a 250 ml three-necked flask fitted with magnetic stirrer, nitrogen/vacuum connection and 25 ml dropping funnel (with pressure equalization). After the mixture had been cooled to 0° C., 10 ml (113 mmol) of trifluoromethanesulfonic acid were added. The mixture was subsequently stirred at room temperature for a further sixteen hours. The solid by-product formed was filtered off with suction and rinsed with n-hexane, and the mother liquor was adjusted to a pH of 8 using sodium hydroxide solution (2.5 N) and finally freed from organic solvent in a rotary evaporator. After taking-up in dichloromethane, the product solution was dried over magnesium sulfate. After removal of the dichloromethane, the product was isolated in a yield of 64%.

Workup

  1. customfitted with magnetic stirrer
  2. customThe solid by-product formed
  3. filtrationwas filtered off with suction
  4. washrinsed with n-hexane
  5. customfinally freed from organic solvent in a rotary evaporator
  6. dry with materialthe product solution was dried over magnesium sulfate
  7. customAfter removal of the dichloromethane
  8. customthe product was isolated in a yield of 64%

Sources & evidence

ORD record
ord-ee7438dde63f469f90a57c498960f42a
Source dataset
uspto-grants-2004_02
Patent number
US06695977B2

Reaction notes

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