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CID 406 → tert-Butyl[2,2-Dimethyl-5-(4-octanoylstyryl)-1,3-dioxan-5-yl]carbamate

HRID 1028883
Notes
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Reaction equation

HRID 1028883 reaction equation
P(=O)([O-])[O-].[C:5]([O:9][C:10](=[O:22])[NH:11][C:12]1([CH:20]=O)[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6].[C:23]([O-:26])([O-])=O.[K+].[K+].[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>CN(C=O)C>[C:5]([O:9][C:10](=[O:22])[NH:11][C:12]1([CH:20]=[CH:31][C:30]2[CH:7]=[CH:5][C:6]([C:23](=[O:26])[CH2:33][CH2:29][CH2:30][CH2:31][CH2:13][CH2:12][CH3:17])=[CH:33][CH:29]=2)[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 406CID 406HCID 8028Tetrahydrofuran2×HCID 11430Potassium CarbonateHCID 24754730Tert-butyl (5-formyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamate

Product 1

HCID 123791953tert-Butyl[2,2-Dimethyl-5-(4-octanoylstyryl)-1,3-dioxan-5-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of the Wittig reagent (23, X═O) or the phosphonate (0.3 mmol), aldehyde (24) (0.33 mmol), and K2CO3 (0.9 mmol) in a mixture of THF (3 ml) and DMF (1 ml) was heated at 70-75° C. under TLC and HPLC monitoring. After completion of the reaction, THF was evaporated and the reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. After purification, the title compound (26) was recovered as white solid with 72% yield, mp 82-83° C.

Workup

  1. customwas evaporated
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customAfter purification
  9. customthe title compound (26) was recovered as white solid with 72% yield, mp 82-83° C.

Sources & evidence

ORD record
ord-51e2f1efc7c34241b66e8e50c59a693e
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735627B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes