Triphenylcarbinol → HCID 178526183, compound

HRID 1591853Notes

Reaction equation

HRID 1591853 reaction equation
C(C[S:7]SCCCC(O)=O)CC(O)=O.[O:15]1[CH2:20][CH2:19]OCC1.C(P(CC[CH2:32][CH3:33])CCCC)CCC.[C:34]1([C:40]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C.O>[C:40]([CH2:32][CH2:33][CH2:19][C:20]([OH:15])=[S:7])([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 6457TriphenylcarbinolHCID 13831TributylphosphineHCID 312751,4-DioxaneHCID 76196Butanoic acid, 4,4'-dithiobis-

Product 1

HCID 178526183HCID 178526183, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.48 g (2 mmol) 4,4-dithiodibutyric acid in freshly distilled dioxane (20 ml) was stirred under a nitrogen atmosphere. Then 0.52 ml (2.1 mmol) tributylphosphine and 50 μl water were added and the reaction mixture was stirred for 4 hours at room temperature. After removing the solvents in vacuo the crude product was dissolved in 25 ml DMF together with 1.15 g (4.4 mmol) triphenylmethanol, and the solution was stirred for 30 minutes at 60° C. After the solution was cooled to ambient temperature, 580 μl (4.6 mmol) borontrifluor etherate was added and the reaction mixture was stirred overnight at 80° C. The solution was concentrated in vacuo and the product purified by column chromatography (silica, eluent: ethyl acetate/hexane 1:1 v/v). After recrystalization from ethyl acetate/hexane the product was obtained as white needles with a yield of 50%.

Workup

  1. customAfter removing the solvents in vacuo the crude product
  2. stirringthe solution was stirred for 30 minutes at 60° C
  3. temperatureAfter the solution was cooled to ambient temperature
  4. addition580 μl (4.6 mmol) borontrifluor etherate was added
  5. stirringthe reaction mixture was stirred overnight at 80° C
  6. concentrationThe solution was concentrated in vacuo
  7. customthe product purified by column chromatography (silica, eluent: ethyl acetate/hexane 1:1 v/v)
  8. customAfter recrystalization from ethyl acetate/hexane the product
  9. customwas obtained as white needles with a yield of 50%

Sources & evidence

ORD record
ord-7f9c6a1167ee4484b2d2d43799d3b0d4
Source dataset
uspto-grants-2007_11
Patent number
US07291673B2

Reaction notes

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