2-Butene-1,4-diol → (Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-ol

HRID 1032909Notes

Reaction equation

HRID 1032909 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:12])[CH:8]=[CH:9][CH2:10][OH:11].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl.O1CCCC1>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:11][CH2:10]/[CH:9]=[CH:8]\[CH2:7][OH:12]

Participants

5

Reactant 3

HCID 80652-Butene-1,4-diolHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 10975949(Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-olYield 481.9%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dihydropyrane (9.1 ml, 100 mmol) was added dropwise to a cooled (0° C.) solution of 2-butene-1,4-diol (8.8 g, 10 mmol) and pyridinium paratoluenesulfonate (0.25 g, 10 mmol) in anhydrous dichloromethane:tetrahydrofuran (2:1). The mixture was stirred two days at 0° C. then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexane 3:7) to give 8.3 g of the title compound (49%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (ethyl acetate:hexane 3:7)

Sources & evidence

ORD record
ord-87867444b2bc4c5b9fe2dd7ddd3d0478
Source dataset
uspto-grants-1994_05
Patent number
US05308837

Reaction notes

Loading…