Benzoic Acid → 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)cyclopropyl benzoate

HRID 1517913Notes

Reaction equation

HRID 1517913 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1([OH:13])[CH2:12][CH2:11]1.[C:14](O)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:14]([O:13][C:10]1([CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:11][CH2:12]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 666697531-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)cyclopropanol

Product 1

HCID 666699361-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)cyclopropyl benzoateYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)cyclopropanol (730 mg, 4.05 mmol) and benzoic acid (590 mg, 4.86 mmol) in 30 mL of CH2Cl2 was added DMAP (98.8 mg, 0.81 mmol, Shanghai Haiqu chemical Ltd.) and EDCI (1.16 g, 6.08 mmol, Shanghai Haiqu chemical Ltd.) at rt. The reaction mixture was stirred at rt overnight, then concentrated and purified by a silica gel column chromatography (20:1 (v/v) petroleum ether/EtOAc)) to afford the title compound as colorless oil (690 mg, 60%).

Workup

  1. concentrationconcentrated
  2. custompurified by a silica gel column chromatography (20:1 (v/v) petroleum ether/EtOAc))

Sources & evidence

ORD record
ord-9e12b11de6b646dc9c189045eda890f5
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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