Triethylamine → HCID 22171593, compound

HRID 1866172Notes

Reaction equation

HRID 1866172 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:56]([O:59][CH2:60][CH3:61])(=[O:58])C>CN(C)C=O.C(O)C.O>[OH:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[CH:9][CH:8]=[C:7]2[C:56]([O:59][CH2:60][CH3:61])=[O:58]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 22171450HCID 22171450, compound

Product 1

HCID 22171593HCID 22171593, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-hydroxy-1-naphthyl trifluoromethane-sulfonate (8.0 g) in N,N-dimethylformamide (35 ml) and ethanol (5.0 ml) were added 1,3-bis(diphenylphosphino)-propane (621 mg), palladium acetate(II) (3.7 mg) and triethylamine (1.35 g), and the mixture was stirred at 100° C. for 1 hour under carbon-monoxide. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=5/1) to give ethyl 5-hydroxy-1-naphthoate (1.7 g) as a colorless oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-c429f66a2c80419794a454f37ebf4a62
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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