Benzyl Alcohol → Benzyl 2-(tetrahydro-2H-pyran-4-yl)acetate

HRID 1774394Notes

Reaction equation

HRID 1774394 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.CCCCCC.C(OCC)(=O)C>ClCCl.O>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 2773575Tetrahydropyran-4-ylacetic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 59706533Benzyl 2-(tetrahydro-2H-pyran-4-yl)acetateYield 32.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(tetrahydropyran-4-yl)acetic acid (325 mg, 2.26 mmol) in anhydrous dichloromethane (10 mL) were added benzyl alcohol (439 mg, 2.94 mmol), 1-ethyl-3-(3-dimethylammoniumpropyl)carbodiimide hydrochloride (564 mg, 2.94 mmol) and triethylamine (297 mg, 2.94 mmol) at room temperature, and the mixture was stirred for 12 h. The reaction mixture was diluted with water (1 mL) to separate the phases, and the organic layer was further washed with water (1 mL) and brine (1 mL). The organic layer was concentrated under reduced pressure, and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 7:1) to give 172 mg of the title compound as oil (yield: 32%).

Workup

  1. customto separate the phases
  2. washthe organic layer was further washed with water (1 mL) and brine (1 mL)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue thus obtained

Sources & evidence

ORD record
ord-abaa8317496044f69a584a24c608bbee
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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