Methyl 1-hydroxy-1-cyclopropane carboxylate → HCID 59354788, compound

HRID 1776314Notes

Reaction equation

HRID 1776314 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](Cl)=[O:21])=[CH:15][CH:14]=1.[OH:23][C:24]1([C:27]([O:29][CH3:30])=[O:28])[CH2:26][CH2:25]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:23][C:24]2([C:27]([O:29][CH3:30])=[O:28])[CH2:26][CH2:25]2)=[O:21])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 2733178Methyl 1-hydroxy-1-cyclopropane carboxylateHCID 59354817HCID 59354817, compound

Product 1

HCID 59354788HCID 59354788, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-(quinolin-2-ylmethoxy)phenyl)acetyl chloride (2.0 g, 6.557 mmol) in DCM (50 mL) was added DMAP (1.4 g, 13.11 mmol) followed by methyl 1-hydroxycyclopropanecarboxylate (1.1 g, 9.836 mmol) under a nitrogen atmosphere at RT. The reaction mixture was stirred for 14 h and after complete consumption of the starting material (by TLC), the reaction mixture was quenched with water (10 mL) and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were washed with a saturated NaHCO3 solution (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford crude methyl 1-(2-(4-(quinolin-2-ylmethoxy)phenyl)acetoxy)cyclopropanecarboxylate (2.0 g) as a solid.

Workup

  1. customafter complete consumption of the starting material (by TLC)
  2. customthe reaction mixture was quenched with water (10 mL)
  3. extractionthe aqueous layer was extracted with DCM (2×50 mL)
  4. washThe combined organic layers were washed with a saturated NaHCO3 solution (20 mL) and brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-710d408fa0b54097bc4a8a805c856869
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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