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

HRID 418756Notes

Reaction equation

HRID 418756 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-6ef58ff63fdd4c5588d883b79c2d4e1f
Source dataset
uspto-grants-2012_01
Patent number
US08093294B2

Reaction notes

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