Methyl chloroacetate → HCID 59841575, compound

HRID 1894681Notes

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 (24.8 g) described in Manufacturing Example 1-1-2 and tetrahydrofuran (160 mL) was added methyl chloroacetate (10.2 mL) at −15° C., and then sodium methoxide (23.7 mL, 28% methanol solution) was added thereto at the same temperature. The reaction mixture was stirred for 1 hour at 0° C., and then stirred for 2 hours at room temperature. The reaction mixture was added to 800 mL of an ice water containing acetic acid (6 mL), and the reaction mixture was warmed to room temperature. Ethyl acetate was added to the reaction mixture for extraction, and then the organic layer was separated, washed with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure to obtain the title compound (30.2 g).

Workup

stirringstirred for 2 hours at room temperature
temperaturethe reaction mixture was warmed to room temperature
customthe organic layer was separated
washwashed with saturated saline
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record: ord-3e2112972d5e4be393f763b54d7ed306
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513287B2

Reaction notes

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