3,4-dihydro-2H-pyran → 5-Bromo-2-propyl-4-(((2-tetrahydropyranyl)oxy)methyl)oxazole

HRID 235090Notes

Reaction equation

HRID 235090 reaction equation
[Br:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][CH3:9])=[N:4][C:3]=1[CH2:10][OH:11].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][CH3:9])=[N:4][C:3]=1[CH2:10][O:11][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:12]1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 233535725-Bromo-2-propyl-4-oxazolemethanol

Product 1

HCID 233535735-Bromo-2-propyl-4-(((2-tetrahydropyranyl)oxy)methyl)oxazoleYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.96 g (8.91 mmol) of the compound from step 29b in 55 mL of methylene chloride at room temperature were sequentially added 7 mL of 3,4-dihydro-2H-pyran (76.7 mmol) and 1 g (3.98 mmol) of PPTS. The reaction was stirred at room temperature for 20 min, 30 mL of satd. NaHCO3 was added, and the mixture was stirred for 5 min. The organic layer was separated, and the aqueous layer was extracted with 2×50 mL of methylene chloride. The organics were combined, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 10-30% ethyl acetate in hexane, to afford, after removal of the solvent and drying, 2.70 g (100% yield) of the title product as a colorless oil. NMR (CDCl3) δ:4.75 (t, J=3 Hz, 1H), 4.57 and 4.33 (ABq, J=12 Hz, 2H), 3.93 (m, 1H), 3.56 (m, 1H), 2.72 (t, J=8 Hz, 2H), 190-1.48 (m, 8H), 1.00 (t, J=8 Hz, 3H).

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred for 5 min
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 2×50 mL of methylene chloride
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with 10-30% ethyl acetate in hexane
  9. customto afford
  10. customafter removal of the solvent
  11. customdrying

Sources & evidence

ORD record
ord-5bf9800a69ec4fd787e9810e076b22d2
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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