Methyl chloroacetate → HCID 59841575, compound

HRID 557267Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.O1CCCC1.Cl[CH2:23][C:24]([O:26][CH3:27])=[O:25].C[O-].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]2[O:14][CH:23]2[C:24]([O:26][CH3:27])=[O:25])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 4-(pyridin-2-yloxymethyl)-benzaldehyde described in Preparation Example 1-3-2 (24.8 g) and tetrahydrofuran (160 mL) was added methyl chloroacetate (10.2 mL) at −15° C, and sodium methoxide (23.7 mL, 28% methanol solution) was then added thereto at the same temperature. The reaction mixture was stirred at 0° C for one hour, and then was stirred for two hours at room temperature. The reaction mixture was added to ice water (800 mL) containing acetic acid (6 mL), and the reaction mixture was allowed to room temperature. To the reaction mixture was added ethyl acetate, and extracted, then, the organic layer was separated, washed with saturated sodium chloride water, and dried over anhydrous magnesium sulfate. The solvent thereof was evaporated under a reduced pressure to obtain the title compound (30.2 g).

Workup

stirringwas stirred for two hours at room temperature
customwas allowed to room temperature
extractionextracted
customthe organic layer was separated
washwashed with saturated sodium chloride water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent thereof was evaporated under a reduced pressure

Sources & evidence

ORD record: ord-9d72e1e36d4c4d1cabd7f8038642f588
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058444B2

Reaction notes

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