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

HRID 1517905Notes

Reaction equation

HRID 1517905 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1([OH:12])[CH2:11][CH2:10]1.[C:13](O)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:13]([O:12][C:9]1([CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:10][CH2:11]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 105591141-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol

Product 1

HCID 666699701-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl benzoateYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol (1.6 g, 9.3 mmol) and benzoic acid (1.25 g, 11.16 mmol, Shanghai Haiqu chemical Ltd.) in 50 mL of CH2Cl2 was added DMAP (227 mg, 1.86 mmol, Shanghai Haiqu chemical Ltd.) and EDCI (2.73 g, 14.25 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 (1.8 g, 70%).

Workup

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

Sources & evidence

ORD record
ord-8d30c9761cfd41e886e277b02d5bf6fe
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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