3,4-dihydro-2H-pyran → HCID 68182046, compound

HRID 1398593Notes

Reaction equation

HRID 1398593 reaction equation
[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8](=[O:10])[CH3:9])[CH:4]=1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.CC1C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.O>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8](=[O:10])[CH3:9])[CH:4]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyran2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 105587091-(5-(Hydroxymethyl)isoxazol-3-yl)ethanone

Product 1

HCID 68182046HCID 68182046, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[5-(hydroxymethyl)-1,2-oxazol-3-yl]ethanone (252 mg, 1.79 mmol), 3,4-dihydro-2H-pyran (0.24 ml, 2.68 mmol) and pyridinium 4-methylbenzenesulfonate (44.69 mg, 0.18 mmol) in DCM (10 mL) was stirred at RT for 16 hr and then for a further 0.5 hr at 40° C. after the addition of more 3,4-dihydro-2H-pyran (0.24 ml, 2.68 mmol) and pyridinium 4-methylbenzenesulfonate (44.69 mg, 0.18 mmol). The reaction mixture was diluted with water (5 ml) and the solution extracted with DCM (2×20 ml). The combined organic layers were washed with brine (5 ml), dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography (Isolute, 9:1 heptane:EtOAc) to give the title intermediate: 1H NMR (500 MHz, CDCl3) delta 1.56-1.53 (2H, m), 1.68-1.60 (2H, m), 1.89-1.69 (2H, m), 2.65 (3H, s), 3.62-3.51 (1H, m), 3.93-3.78 (1H, m), 4.68 (1H, d, J=13.9 Hz), 4.75 (1H, t, J=3.3 Hz), 4.86-4.80 (1 H, m), 6.63 (1H, s).

Workup

  1. extractionthe solution extracted with DCM (2×20 ml)
  2. washThe combined organic layers were washed with brine (5 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography (Isolute, 9:1 heptane:EtOAc)

Sources & evidence

ORD record
ord-89a28364f36b4a9db8f79496cff357cd
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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