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Dimethylformamide → Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetate

HRID 530929
Notes
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Reaction equation

HRID 530929 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].CN(C)C=O.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:24][CH:23]=1>O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:27][CH:26]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

Product 1

HCID 68357704Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetateYield 98.3%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Potassium carbonate (1.38 g) and tert-butyl bromoacetate (1.07 g) were added to a dehydrated N,N-dimethylformamide (17 mL) solution of benzyl (4-hydroxyphenyl)acetate (1.21 g) at room temperature, followed by stirring for 1 hour. Thereafter, water was added to the reaction mixture on an ice bath, and extraction was performed with hexane:ethyl acetate=2:1. The resulting organic phase was washed with an aqueous saturated sodium chloride solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→8:2) to obtain the title compound (1.75 g) having the following physical property values.

Workup

  1. extractionextraction
  2. washThe resulting organic phase was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→8:2)

Sources & evidence

ORD record
ord-4bb030380e974bc88169e9b0d50458a6
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09353113B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes