3,4-dihydro-2H-pyran → benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate

HRID 1517911Notes

Reaction equation

HRID 1517911 reaction equation
[OH:1][CH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[CH2:14]1[CH2:19][O:18][CH:17]=[CH:16][CH2:15]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>ClCCl>[O:18]1[CH2:19][CH2:14][CH2:15][CH2:16][CH:17]1[O:1][CH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 84459Propanoic acid, 3-hydroxy-, phenylmethyl esterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 66669830benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoateYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzyl 3-hydroxypropanoate (3.35 g, 18.6 mmol) and DHP (3.12 g, 37.2 mmol, Alfa) in dichloromethane (100 mL) was added PPTS (5.6 g, 22.3 mmol, Aldrich) in portions. The reaction mixture was stirred at rt overnight, and was quenched with 50 mL of H2O. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (10:1 (v/v) petroleum ether/EtOAc) to give the title compound as colorless oil (4.25 g, 86%).

Workup

  1. customwas quenched with 50 mL of H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (10:1 (v/v) petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-c024c96bd68f42a2856ca7702c21eb3b
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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