3,4-dihydro-2H-pyran → 2H-Pyran, tetrahydro-2-(4-iodophenoxy)-

HRID 1191965Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1>C(Cl)Cl.C1(C)C(S(O)(=O)=O)=CC=CC=1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred solution of 4-iodophenol (11.0 g, 50 mmol) in CH2Cl2 (50 ml) cooled with an ice bath, dihydropyran (5.0 g, 60 mmol) was added dropwise over 10 min at 0° C. to 5° C. After the solution became clear, toluenesulfonic acid (TsOH′ 10 mg) was added. The solution was stirred at 20° C. for 15 min. Then it was quenched by addition of NaHCO3 (1 g) and 3 drops of water, and after stirring for 5 min at 20° C., the solvent was removed in vacuo and the residue was purified by column chromatography on silica gel with petroleum ether as eluent to give 14.0 g (92%) of 1 as colorless crystal; mp 66° C.; δH(CDCl3, 300 MHz): 7.55 (d, J=8.3, 2H, Ar—H), 6.83 (d, J=8.4, 2H, Ar—H), 5.37 (t, J=3.1, 1H, OCHO), 3.86 (m, 1H, THP), 3.59 (m, 1H, THP), 1.87˜1.58 (m, 6H, THP).

Workup

customThen it was quenched by addition of NaHCO3 (1 g) and 3 drops of water
stirringafter stirring for 5 min at 20° C.
customthe solvent was removed in vacuo
customthe residue was purified by column chromatography on silica gel with petroleum ether as eluent

Sources & evidence

ORD record: ord-80b87373644b4884b9fc37c1f57b69f8
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680142B2

Reaction notes

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