Triethylamine → HCID 21458935, compound

HRID 725288Notes

Reaction equation

HRID 725288 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([S:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:21]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:20]=2)=O)[CH:9]=[CH:10][C:11]=1[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[O:42]([Si](C)(C)C)[S:43]([C:46]([F:49])([F:48])[F:47])(=[O:45])=[O:44].[C:54]([O:58][C:59]1[CH:64]=[CH:63][C:62](Cl)=[CH:61][C:60]=1[O:66][C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:57])([CH3:56])[CH3:55].[Mg].[Cl-].[NH4+]>C1COCC1.C(Cl)(Cl)Cl.CO>[F:47][C:46]([F:49])([F:48])[S:43]([O-:45])(=[O:44])=[O:42].[C:1]([O:5][C:6]1[CH:7]=[C:8]([S+:17]([C:63]2[CH:62]=[CH:61][C:60]([O:66][C:67]([CH3:68])([CH3:69])[CH3:70])=[C:59]([O:58][C:54]([CH3:57])([CH3:56])[CH3:55])[CH:64]=2)[C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:21]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:20]=2)[CH:9]=[CH:10][C:11]=1[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65367Trimethylsilyl triflateHCID 5462224MagnesiumHCID 21458933HCID 21458933, compoundHCID 538105471,1'-Sulfinylbis(3,4-di-tert-butoxybenzene)

Product 1

HCID 21458935HCID 21458935, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

A Grignard reagent was conventionally prepared using 3,4-di-tert-butoxyphenyl chloride, magnesium, and THF and further reacted with thionyl chloride, obtaining bis(3,4-di-tert-butoxyphenyl) sulfoxide in a yield of 64%. Then 58.9 g (0.12 mol) of bis(3,4-di-tert-butoxyphenyl) sulfoxide was dissolved in 120 g of THF and cooled in an ice water bath. Then 12.1 g (0.12 mol) of triethylamine was added thereto and 68.3 g (0.31 mol) of trimethylsilyl triflate was added dropwise in a controlled manner at less 10° C. To this solution, a Grignard reagent which was conventionally prepared using 61.6 g (0.24 mol) of 1,2-di-tert-butoxy-4-chlorobenzene, 5.8 g (0.24 mol) of magnesium, and 100 g of THF was added dropwise in a controlled manner at less 10° C. With the reaction temperature controlled at 0° to 10° C., reaction ripening was carried out for 30 minutes. A 20% ammonium chloride aqueous solution, 700 g, was added to the reaction solution to terminate reaction, followed by separation. 300 g of chloroform was added to the organic layer. The organic layer was washed twice using 300 g of water and then evaporated, obtaining an oily residue. The oily residue was worked up by column chromatography (silica gel, eluent: chloroform/methanol), obtaining tris(3,4-di-tert-butoxyphenyl)sulfonium trifluoromethanesulfonate of 99% purity in a yield of 20%. The final percent yield of this two-steps synthesis process was 13%.

Workup

  1. temperaturecooled in an ice water bath
  2. additionwas added dropwise in a controlled manner at less 10° C
  3. customcontrolled at 0° to 10° C.
  4. customreaction ripening
  5. customto terminate
  6. customreaction
  7. customfollowed by separation
  8. addition300 g of chloroform was added to the organic layer
  9. washThe organic layer was washed twice
  10. customevaporated
  11. customobtaining an oily residue

Sources & evidence

ORD record
ord-804c62cdfd934b2999ea2ec3ec273b86
Source dataset
uspto-grants-1998_01
Patent number
US05705702

Reaction notes

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