Tributylphosphine → HCID 66777532, compound

HRID 2091330Notes

Reaction equation

HRID 2091330 reaction equation
[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:12]=3[C:13]=2[CH3:14])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:20][S:21][CH2:22][CH2:23]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([O:19][CH2:23][CH2:22][S:21][CH3:20])=[CH:15][C:12]=3[C:13]=2[CH3:14])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 789252-(Methylthio)ethanolHCID 66777135HCID 66777135, compound

Product 1

HCID 66777532HCID 66777532, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexyl(5-hydroxy-3-methyl-1-benzofuran-2-yl)methanone (0.76 g) synthesized in Example A82(3) was dissolved in tetrahydrofuran (15 mL), and 2-(methylthio)ethanol (0.26 mL), tributylphosphine (1.5 mL) and 1,1′-(azodicarbonyl)dipiperidine (1.46 g) were added to the solution under ice-cooling. The ice bath was removed, and the reaction mixture was stirred at room temperature for 12 hr. Hexane (15 mL) was added to the mixture, and the precipitate was filtered off through celite. Water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (0.73 g, 76%) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. customThe ice bath was removed
  3. additionHexane (15 mL) was added to the mixture
  4. filtrationthe precipitate was filtered off through celite
  5. additionWater was added to the filtrate
  6. extractionthe mixture was extracted with ethyl acetate
  7. concentrationThe extract was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record
ord-bac6445a30854b3e8b91fe8fcdd1490c
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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