HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethyl formate → Benzyl 2-chloro-3-oxopropanoate

HRID 79318
Notes
Print preview

Reaction equation

HRID 79318 reaction equation
C[C:2](C)([O-:4])C.[K+].[Cl:7][CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C(OCC)=O>CCOCC>[Cl:7][CH:8]([CH:2]=[O:4])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 8786Acetic acid, 2-chloro-, phenylmethyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 86672210Benzyl 2-chloro-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To potassium tert-butoxide (141 mL, 141 mmol) at 0° C. was added dropwise a solution of benzyl 2-chloroacetate (26.8 g, 141 mmol) and ethyl formate (11.6 mL, 141 mmol) in Et2O (45 mL). The reaction was warmed to ambient temperature and stirred for 16 hours. The reaction mixture was filtered and washed with cold ether (100 mL). The potassium salt was dissolved in H2O (50 mL) and the solution was acidified with concentrated HCl to pH=4 in a cold bath. The solution was extracted with ether and the organic phase was dried (MgSO4) and concentrated to give the crude product. A lower boiling point impurity was removed by vacuum distillation (90° C., 5 mm Hg) and the residue was taken directly to the next step.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with cold ether (100 mL)
  3. dissolutionThe potassium salt was dissolved in H2O (50 mL)
  4. customthe solution was acidified with concentrated HCl to pH=4 in a cold bath
  5. extractionThe solution was extracted with ether
  6. dry with materialthe organic phase was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cd736840933d49b08d4e6330be5fe87d
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841455B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes