Carbon Dioxide → HCID 59541844, compound

HRID 2388346Notes

Reaction equation

HRID 2388346 reaction equation
[Li]CCCC.[O:6]1[C:10]2([CH2:15][CH2:14][CH:13]([C:16]3[S:17][CH:18]=[CH:19][N:20]=3)[CH2:12][CH2:11]2)[O:9][CH2:8][CH2:7]1.[C:21](=[O:23])=[O:22]>C1COCC1>[O:9]1[C:10]2([CH2:15][CH2:14][CH:13]([C:16]3[S:17][C:18]([C:21]([OH:23])=[O:22])=[CH:19][N:20]=3)[CH2:12][CH2:11]2)[O:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 595560502-(1,4-Dioxa-spiro[4.5]dec-8-yl)-thiazoleHCID 178418339Butyllithium

Product 1

HCID 59541844HCID 59541844, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-BuLi (2.5 M in hexanes, 5 mL, 12 mmol) was added dropwise into 2-(1,4-dioxa-spiro[4.5]dec-8-yl)-thiazole (2.50 g, 11 mmol) in THF (10 mL) at −78° C. The reaction was kept at −78° C. for 30 min. The solution was added to solid dry ice (˜5 g) dropwise. After addition, the reaction was warmed to room temperature slowly over 1 hour and quenched with 1 N NaOH (˜10 mL) solution. The solvent was removed and the residue was partitioned between ether and water. The aqueous layer was adjusted to pH=6 with 5% HCl and extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title compound as white solid.

Workup

  1. additionAfter addition
  2. customquenched with 1 N NaOH (˜10 mL) solution
  3. customThe solvent was removed
  4. customthe residue was partitioned between ether and water
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c5c3e07a3cd244db9a2ee25d21d325d2
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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