Benzyl Bromide → benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate

HRID 1969386Notes

Reaction equation

HRID 1969386 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]([O:12][CH2:19][C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)=[O:11]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 552690473-[(2-Tetrahydropyranyl)oxy]propanoic acid

Product 1

HCID 66669830benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoateYield 18.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(tetrahydro-2H-pyran-2-yloxy) propanoic acid (1 g, 5.7 mmol) and TEA (0.863 g, 8.55 mmol, Shantou Xilong chemical factory) in 50 mL of CH2Cl2 was added BnBr (0.98 g, 5.7 mmol, Aldrich) via a syringe at 0° C. After stirring at rt overnight, the reaction mixture was quenched with 20 mL of water, and was extracted with ethyl acetate (50 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (20:1 (v/v) petroleum ether/EtOAc) to give the title compound as colorless oil (270 mg, 18.6%).

Workup

  1. customthe reaction mixture was quenched with 20 mL of water
  2. extractionwas extracted with ethyl acetate (50 mL×3)
  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 (20:1 (v/v) petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-1322f3a9bc9745fbad8c073e6395fba7
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

Loading…