3,4-dihydro-2H-pyran → 2-[2-Bromo-3-(4-methoxy-benzyloxy)-benzyloxy]-tetrahydro-pyran

HRID 339623Notes

Reaction equation

HRID 339623 reaction equation
[CH2:1]1[CH2:6][O:5][CH:4]=[CH:3][CH2:2]1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[Br:22][C:23]1[C:28]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:39][OH:40].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:22][C:23]1[C:28]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:39][O:40][CH:4]1[CH2:3][CH2:2][CH2:1][CH2:6][O:5]1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium BicarbonateHCID 59515252[2-Bromo-3-(4-methoxy-benzyloxy)-phenyl]-methanol

Product 1

HCID 595152152-[2-Bromo-3-(4-methoxy-benzyloxy)-benzyloxy]-tetrahydro-pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DHP (0.67 mL, 7.4 mmol) and CSA (30 mg, 0.12 mmol) were added to a solution of [2-bromo-3-(4-methoxy-benzyloxy)-phenyl]-methanol (2.0 g, 6.1 mmol) in CH2Cl2 (15 mL). The resulting mixture was stirred at rt O/N. 4 Å Molecular sieves (1.0 g) was added and mixture was stirred for 1 h. Sat. NaHCO3 was added and mixture was extracted with CHCl3 (2×50 mL). The organic fractions were washed with H2O (2×25 mL) then brine (50 mL), dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (25% EtOAc in hexane) to give the title compound as yellow oil: yield 1.30 g (96%).

Workup

  1. addition4 Å Molecular sieves (1.0 g) was added
  2. stirringmixture was stirred for 1 h
  3. extractionmixture was extracted with CHCl3 (2×50 mL)
  4. washThe organic fractions were washed with H2O (2×25 mL)
  5. dry with materialbrine (50 mL), dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-f2c0ab3502a0443089dbccdba7ead84c
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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