Triethylamine → 3-Dipropylamino-5-methyloxycarbonylchroman

HRID 2257337Notes

Reaction equation

HRID 2257337 reaction equation
[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2S(C(F)(F)F)(=O)=O)[O:7][CH2:6]1)[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CN(C)[CH:63]=[O:64].[CH3:66][OH:67]>C1(C)C=CC=CC=1>[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:66]([O:64][CH3:63])=[O:67])[O:7][CH2:6]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 19028106HCID 19028106, compoundHCID 21901440N,N-dimethylformamide methanol

Product 1

HCID 190280933-Dipropylamino-5-methyloxycarbonylchroman

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

3-Dipropylamino-5-trifluoromethanesulfonylchroman (Example 1; 4.43 g, 11.6 mmol) was dissolved in 80 mL dimethylformamide/methanol 6:2 and the solution was degassed (10 mm Hg, 20° C., 15 min). PdOAc2 (76 mg, 0.34 mmol), 1,3-bis-diphenylphosphinopropane (141 mg, 0.34 mmol) and triethylamine (3.5 mL, 25 mmol) were then added. The mixture was heated to 70° C. under CO atmosphere and stirred for 5 hours. The solution was cooled, diluted with toluene (200 mL), washed with aqueous NaHCO3, dried with Na2SO4 and evaporated to dryness. The oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8.

Workup

  1. customthe solution was degassed (10 mm Hg, 20° C., 15 min)
  2. temperatureThe solution was cooled
  3. washwashed with aqueous NaHCO3
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness
  6. customThe oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8

Sources & evidence

ORD record
ord-2559234cbdd44f0d83c9e2776377f857
Source dataset
uspto-grants-1997_08
Patent number
US05656658

Reaction notes

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