3,4-dihydro-2H-pyran → 2-[(4-bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methoxy]tetrahydro-2H-pyran

HRID 870048Notes

Reaction equation

HRID 870048 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Br:18][C:19]1[C:20]([CH:26]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[OH:27])=[C:21]([Cl:25])[S:22][C:23]=1[Cl:24].[O:35]1[CH:40]=[CH:39][CH2:38][CH2:37][CH2:36]1>C(Cl)Cl.C(Cl)(Cl)Cl>[Br:18][C:19]1[C:20]([CH:26]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[O:27][CH:36]2[CH2:37][CH2:38][CH2:39][CH2:40][O:35]2)=[C:21]([Cl:25])[S:22][C:23]=1[Cl:24]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57900988(4-Bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methanol

Product 1

HCID 579009842-[(4-bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methoxy]tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Pyridinium p-toluenesulfonate (74.0 mg, 0.293 mmol) was added to (4-bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methanol from Example 8, Step 1 (1.09 g, 2.93 mmol) and 3,4-dihydro-2H-pyran (2.67 mL, 29.3 mmol) in CH2Cl2 (12 mL). After 3.5 h, the reaction mixture was diluted with CHCl3 and washed with 5% aq. NaHCO3, water and brine, dried (Na2SO4) and concentrated. The crude product was purified by Combi Flash chromatography system (30-50% CHCl3/hexane in 20 min.) to afford the desired product as a colorless gum.

Workup

  1. washwashed with 5% aq. NaHCO3, water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by Combi Flash chromatography system (30-50% CHCl3/hexane in 20 min.)

Sources & evidence

ORD record
ord-e7dfba7847f2449686a5f9a138aa0e01
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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