Triethylamine → HCID 54309784, compound

HRID 376530Notes

Reaction equation

HRID 376530 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([SH:16])[CH:13]=[CH:14][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[CH2:43][CH:44]=[O:45]>O.O1CCCC1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([S:16][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]2[CH2:43][CH:44]=[O:45])[CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 849893-MethoxybenzenethiolHCID 54554648HCID 54554648, compound

Product 1

HCID 54309784HCID 54309784, compoundYield 134.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine 481 ml is added to the mixture of 3-methoxythiophenol 322.5 g, triphenylphosphine 241.3 g, water 204 ml and tetrahydrofuran 2.3 liter under nitrogen atmosphere while cooling with ice under stirring, and then 2-bromocyclohexylacetaldehyde 518.9 g is dropwise added. Stirring is carried out at a room temperature for one hour, and then stirring is further continued at 60° C. for 2.5 hours. Water 200 ml is added, and the mixture is shaken. The organic layer is separated and washed twice with 10% hydrochloric acid 500 ml and twice with saturated brine 400 ml, and then it is dried on magnesium sulfate anhydrous. The solvent is distilled off under reduced pressure, and the residue is dissolved in hexane 2 liter and stirred at a room temperature for 13 hours. After cooling with ice, deposited crystals are filtered off, and the solvent is distilled off under reduced pressure, whereby yellow oily 2-(3-methoxyphenylthio)cyclohexylacetaldehyde 820.3 g is obtained.

Workup

  1. temperaturewhile cooling with ice
  2. stirringStirring
  3. stirringstirring
  4. waitis further continued at 60° C. for 2.5 hours
  5. stirringthe mixture is shaken
  6. customThe organic layer is separated
  7. washwashed twice with 10% hydrochloric acid 500 ml and twice with saturated brine 400 ml
  8. customit is dried on magnesium sulfate anhydrous
  9. distillationThe solvent is distilled off under reduced pressure
  10. dissolutionthe residue is dissolved in hexane 2 liter
  11. stirringstirred at a room temperature for 13 hours
  12. temperatureAfter cooling with ice
  13. filtrationare filtered off
  14. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-81974f352c3b488285c823b1fbc5fafc
Source dataset
uspto-grants-2000_02
Patent number
US06020531

Reaction notes

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