3,4-dihydro-2H-pyran → HCID 89619898, compound

HRID 714600Notes

Reaction equation

HRID 714600 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([OH:18])=[C:10]([C:15](=[O:17])[CH3:16])[CH:11]=[C:12]([OH:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:36]1[CH:41]=[CH:40][CH2:39][CH2:38][CH2:37]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:10]2[CH:11]=[C:12]([O:14][CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][O:36]3)[CH:13]=[CH:16][C:15]=2[OH:17])=[O:18])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 117729199HCID 117729199, compound

Product 1

HCID 89619898HCID 89619898, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-(3-bromophenyl)-1-(2,5-dihydroxyphenyl)ethanone (4.79 g, 16.2 mmol) and pyridinium p-toluene sulfonate (815 mg, 3.24 mmol) in DCM (100 mL), 3,4-dihydro-2H-pyran (2.2 mL, 24.1 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and diluted with DCM (100 mL). The solution was washed (100 mL sat'd aqueous NaHCO3), dried (Na2SO4) and concentrated under reduced pressure. The crude material was purified on a silica gel column to give 2-(3-bromophenyl)-1-(2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethanone (5.28 g, 83%) as a yellow solid. 1H NMR (DMSO-d6): δ 11.23 (s, 1H), 7.56 (d, 1H), 7.51 (m, 1H), 7.46 (dt, 1H), 7.32-7.24 (m, 3H), 6.92 (d, 1H), 5.42 (t, 1H), 4.46 (s, 2H), 3.80 (m, 1H), 3.55 (m, 1H), 1.96-1.68 (m, 3H), 1.68-1.48 (m, 3H).

Workup

  1. additionwas added
  2. washThe solution was washed (100 mL sat'd aqueous NaHCO3)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-2eb8521b2ffa405ebb7838b35c8e46f8
Source dataset
uspto-grants-2015_11
Patent number
US09187460B2

Reaction notes

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