Ethyl bromoacetate → HCID 19040982, compound

HRID 2209727Notes

Reaction equation

[C:1]([C:3]1[CH:31]=[CH:30][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[O:19])=[C:16]([OH:29])[CH:15]=2)=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:25])[CH3:26])[CH:21]([CH3:23])[CH3:22])=[O:19])=[C:16]([CH:15]=2)[O:29][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:30][CH:31]=1)#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred solution of 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-N,N-bis(1-methylethyl)benzamide (1.0 g, 2.36 mmol) in 10.0 mL of N,N-dimethylformamide is treated with 60% sodium hydride (100 mg, 2.59 mmol) and ethyl bromoacetate (290 μL, 2.59 mmol), and the mixture is heated at 70° C. overnight; the reaction is partitioned between ethyl acetate and water, dried over sodium sulfate and concentrated in vacuo to afford a yellow foam. This material is purified by chromatography on silica gel (30 g) with 40-50% ethyl acetate/hexane as the eluent to afford ethyl 5-[5-(4-cyanophenoxy )pentyloxy]-2-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxyacetate as a colorless foam.

Workup

customthe reaction is partitioned between ethyl acetate and water
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customto afford a yellow foam
customThis material is purified by chromatography on silica gel (30 g) with 40-50% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record: ord-b6134bcd9f25486b963b9480f9b31f9b
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455274

Reaction notes

Loading…