Triethylamine → HCID 86652132, compound

HRID 2039437Notes

Reaction equation

HRID 2039437 reaction equation
[Na].[OH:2][CH:3]([CH3:20])[CH2:4][CH:5]([S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[S:6]([C:9]([F:12])([F:11])[F:10])(=[O:8])=[O:7].[C:21]12([C:31](Cl)=[O:32])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2.C(N(CC)CC)C.[Cl-].[C:42]1([S+:48]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O.C(#N)C>[C:55]1([S+:48]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1.[C:21]12([C:31]([O:2][CH:3]([CH3:20])[CH2:4][CH:5]([S:6]([C:9]([F:10])([F:11])[F:12])(=[O:7])=[O:8])[S:13]([C:16]([F:18])([F:19])[F:17])(=[O:15])=[O:14])=[O:32])[CH2:28][CH:27]3[CH2:26][CH:25]([CH2:24][CH:23]([CH2:29]3)[CH2:22]1)[CH2:30]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 61343Triphenylsulfonium chlorideHCID 989151-Adamantanecarbonyl chlorideHCID 86652133HCID 86652133, compound

Product 1

HCID 86652132HCID 86652132, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A glass flask was charged with 10 g (0.028 mol) of 3-hydroxy-1,1-bis(trifluoromethanesulfonyl)butane sodium salt, 16.7 g (0.084 mol) of 1-adamantanecarbonyl chloride, and 50 ml of acetonitrile, followed by stirring. Then, 8.6 g (0.084 mol) of triethylamine was added dropwise. After terminating the dropping, stirring was conducted at 55° C. for 4 hr. Then, the reaction liquid suspended was filtered to remove solid, and the solvent was distilled out of the filtrate by an evaporator. Then, 50 ml of chloroform was added to make a solution, and a 50 ml-water solution of 8.3 g (0.028 mol) of triphenylsulfonium chloride was added dropwise. After terminating the dropping, stirring was continued at room temperature for 1 hr. Then, the organic layer of the reaction liquid was washed three times with 40 ml of water, followed by distilling solvent off with an evaporator. The obtained liquid of a pale brown color was further washed three times with 40 ml of diethyl ether, followed by drying with a vacuum pump, thereby obtaining 9.1 g (yield 50%, purity 95%) of 3-(1-adamantanecarbonyl)oxy-1,1-bis(trifluoromethanesulfonyl)butane triphenylsulfonium salt as a pale brown color liquid.

Workup

  1. customAfter terminating the dropping
  2. stirringstirring
  3. customThen, the reaction liquid
  4. filtrationsuspended was filtered
  5. customto remove solid
  6. distillationthe solvent was distilled out of the filtrate by an evaporator
  7. additionThen, 50 ml of chloroform was added
  8. customAfter terminating the dropping
  9. stirringstirring
  10. waitwas continued at room temperature for 1 hr
  11. customThen, the organic layer of the reaction liquid
  12. washwas washed three times with 40 ml of water
  13. distillationby distilling solvent
  14. customoff with an evaporator
  15. washThe obtained liquid of a pale brown color was further washed three times with 40 ml of diethyl ether
  16. customby drying with a vacuum pump

Sources & evidence

ORD record
ord-1c97d37ceb324c59b7eea43c39b93733
Source dataset
uspto-grants-2013_11
Patent number
US08580486B2

Reaction notes

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