Potassium Carbonate → HCID 86303720, compound

HRID 1484807Notes

Reaction equation

HRID 1484807 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=1[CH:10]=[O:11].Cl[CH2:18][C:19]1[CH2:20][CH2:21][N:22]([CH3:31])[CH2:23][C:24]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.CCOC(C)=O>[OH:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:18][C:19]2[CH2:20][CH2:21][N:22]([CH3:31])[CH2:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:9]=1[CH:10]=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 102858012,6-DihydroxybenzaldehydeHCID 90418702HCID 90418702, compound

Product 1

HCID 86303720HCID 86303720, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of K2CO3 (350 mg, 2.56 mmol) and 2,6-dihydroxybenzaldehyde (180 mg, 1.28 mmol) in DMF (3 ml) was added a solution of 4-(chloromethyl)-1-methyl-5-phenyl-1,2,3,6-tetrahydropyridine (140 mg, 0.64 mmol) in DMF (4 mL), the mixture was heated at 50° C. for 3 h, cooled to room temperature, and was diluted with EtOAc, organic layer was separated and aqueous layer was extracted with EtOAc. EtOAc layers were combined, washed with Sat. NaHCO3, brine, dried over Na2SO4, and was concentrated to give crude oil, which was purified by column (Hexane/EtOAc=1:1 followed by DCM/MeOH=90:10) to give 2-hydroxy-6-((1-methyl-5-phenyl-1,2,3,6-tetrahydropyridin-4-yl)methoxy)benzaldehyde (55 mg). 1H NMR (400 MHz, CDCl3) δ (ppm) 11.92 (s, 1H), 10.35 (s, 1H), 7.34 (m, 5H), 7.19 (dd, J=8.4, 8.0 Hz, 1H), 6.46 (d, J=8.4 Hz, 1H), 6.16 (d, J=8.0 Hz, 1H), 4.45 (s, 2H), 3.20 (s, 2H), 2.68 (t, J=5.6 Hz, 2H), 2.47 (m, 2H), 2.42 (s, 3H); MS (ESI) m/z 324.3 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. customwas separated
  3. extractionaqueous layer was extracted with EtOAc
  4. washwashed with Sat. NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationwas concentrated
  7. customto give crude oil, which
  8. customwas purified by column (Hexane/EtOAc=1:1 followed by DCM/MeOH=90:10)

Sources & evidence

ORD record
ord-31739bf6da3d48d4aa68cc4798698704
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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