Carbon Dioxide → HCID 19041638, compound

HRID 1684010Notes

Reaction equation

HRID 1684010 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[C:13]1[CH:14]=[C:15](Br)[CH:16]=[CH:17][CH:18]=1.[Li]CCCC.[C:25](=[O:27])=[O:26].Cl.[N+](=[CH2:31])=[N-]>C1COCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[C:25]([O:27][CH3:31])=[O:26]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 19041703HCID 19041703, compoundHCID 178418339Butyllithium

Product 1

HCID 19041638HCID 19041638, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a -78° C. solution of the bromide (539 mg, 1.7 mmol) from Step 2 in THF (10 mL) was added dropwise n-BuLi (1 .4M, 2.67 mL). After 15 min the mixture was poured over crushed CO2 and allowed to warm up to room temperature. Dilute HCl (25 mL) was added and the product was extracted in ethyl acetate. The organic layer was washed with brine, dried with MgSO4 and the solvents removed to leave a residue which was treated with a slight excess of diazomethane in ether. Removal of the solvent yielded the product (351 mg).

Workup

  1. additionAfter 15 min the mixture was poured
  2. extractionthe product was extracted in ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. customthe solvents removed
  6. customto leave a residue which
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-3da955c663fc43518e6491bb50d647ec
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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