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Ammonium Chloride → Methyl 4-((e)-2-tert-butoxycarbonyl-vinyl)-2-methoxy-benzoate

HRID 222847
Notes
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Reaction equation

HRID 222847 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.C([O-])(C)(C)C.[Na+].[CH:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]([O:35][CH3:36])[CH:26]=1)=O.[Cl-].[NH4+]>O1CCCC1>[C:13]([O:12][C:10](/[CH:9]=[CH:23]/[C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]([O:35][CH3:36])[CH:26]=1)=[O:11])([CH3:14])([CH3:15])[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 18510332Methyl 4-formyl-2-methoxybenzoateHCID 23676156Sodium t-butoxide

Product 1

HCID 23282641Methyl 4-((e)-2-tert-butoxycarbonyl-vinyl)-2-methoxy-benzoate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
0 °C

Procedure

To 720 μL of tert-butyl diethylphosphonoacetate (1.1 equivalents) in 3 mL of tetrahydrofurane cooled to 0° C. under an inert atmosphere are added 307 mg of sodium tert-butanolate (1.15 equivalents). The whole is stirred for 30 minutes at 0° C. and then for 1 hour at room temperature. A solution cooled to 0-4° C. of 540 mg of aldehyde obtained in stage 3 in 1 ml of tetrahydrofurane is added dropwise to the previous mixture also cooled to 0° C. Stirring is maintained at this temperature for 30 minutes before letting the temperature rise back to room temperature for 2 hours. The medium is hydrolyzed with a saturated solution of ammonium chloride and extracted with ethyl acetate several times. The collected organic phases are washed with water, and then dried on magnesium sulfate, filtered and evaporated under reduced pressure. The reaction crude product is purified by chromatography on silica gel (petroleum ether/ethyl acetate: 95/5) leading to 500 mg of the expected product.

Workup

  1. waitfor 1 hour at room temperature
  2. additionis added dropwise to the previous mixture
  3. temperaturealso cooled to 0° C
  4. stirringStirring
  5. temperatureis maintained at this temperature for 30 minutes
  6. customback to room temperature
  7. customfor 2 hours
  8. extractionextracted with ethyl acetate several times
  9. washThe collected organic phases are washed with water
  10. customdried on magnesium sulfate
  11. filtrationfiltered
  12. customevaporated under reduced pressure
  13. customThe reaction crude product
  14. customis purified by chromatography on silica gel (petroleum ether/ethyl acetate: 95/5)

Sources & evidence

ORD record
ord-77ea7f73f1194be8b1358c6d06576aa5
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08207373B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes