3,4-dihydro-2H-pyran → 3-[(2-Tetrahydropyranyl)oxy]propanoic acid

HRID 1969385Notes

Reaction equation

HRID 1969385 reaction equation
[OH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:7]1[CH2:12][O:11][CH:10]=[CH:9][CH2:8]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>ClCCl.C1COCC1>[O:11]1[CH2:12][CH2:7][CH2:8][CH2:9][CH:10]1[O:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 681523-Hydroxypropionic acidHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 552690473-[(2-Tetrahydropyranyl)oxy]propanoic acidYield 56%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-hydroxypropanoic acid (7.2 g, 80 mmol, TCI, TOKYO KASEI) and DHP (13.4 g, 160 mmol, Alfa) in dichloromethane (100 mL) and THF (100 mL) was added PPTS (2 g, 8 mmol, Aldrich) in portions. The reaction mixture was stirred at rt overnight, and was quenched with 50 mL of saturated NaHCO3 aqueous solution. The resulted mixture was extracted with dichloromethane (50 mL×5). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (1:1 (v/v) petroleum ether/EtOAc) to give colorless oil (7.8 g, 56%).

Workup

  1. customwas quenched with 50 mL of saturated NaHCO3 aqueous solution
  2. extractionThe resulted mixture was extracted with dichloromethane (50 mL×5)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (1:1 (v/v) petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-ede2401ba82e4b3d94803e5ef7a4a65f
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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