2-(4-Bromophenoxy)tetrahydro-2H-pyran → HCID 86709387, compound

HRID 2172223Notes

Reaction equation

HRID 2172223 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][C:12]([CH:13]=[C:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)=[CH:25][CH:24]=1.CC(C)([O-])C.[Na+].F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][C:12]([CH:13]=[C:14]2[CH2:19][CH2:18][N:17]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][O:31]4)=[CH:25][CH:24]=3)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 46464362-(4-Bromophenoxy)tetrahydro-2H-pyranHCID 23676156Sodium t-butoxideHCID 44558591Tri-t-butylphosphine fluoroborateHCID 70873356HCID 70873356, compound

Product 1

HCID 86709387HCID 86709387, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-[4-(Benzyloxy)benzylidene]piperidine (2.32 g, 8.3 mmol), 1-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzene (2.35 g, 9.1 mmol), toluene (20 ml), sodium tert-butoxide (1.12 g, 11.6 mmol), palladium acetate (0.075 g, 0.3 mmol) and tri-tert-butylphosphine tetrafluoroborate (0.19 g, 0.7 mmol) were mixed and stirred at 100° C. overnight. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→50:50) to afford the title compound as a colorless powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→50:50)

Sources & evidence

ORD record
ord-eea6b17c9d55479b959159953b418039
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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