Carbon Dioxide → HCID 10957942, compound

HRID 617706Notes

Reaction equation

HRID 617706 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:17])[C:5]2[S:16][CH2:15][CH2:14][C:9]3([S:13][CH2:12][CH2:11][S:10]3)[C:6]=2[C:7]=1[CH3:8].C([Li])CCC.[C:23](=[O:25])=[O:24]>O1CCCC1.CCCCCC>[CH3:8][C:7]1[C:6]2[C:9]3([CH2:14][CH2:15][S:16][C:5]=2[C:4]([CH3:17])=[CH:3][C:2]=1[C:23]([OH:25])=[O:24])[S:13][CH2:12][CH2:11][S:10]3

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 21849015HCID 21849015, compoundHCID 178418339Butyllithium

Product 1

HCID 10957942HCID 10957942, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of the title compound of Step A (2.7 g, 7.7 mmol) in tetrahydrofuran (20 mL) under a nitrogen atmosphere cooled to -78° C. was added n-butyllithium (Aldrich, 4.6 mL, 11.5 mmol of a 2.5 M solution in hexane) dropwise while maintaining the temperature below -60° C. After stirring for 2 h, excess carbon dioxide (dry ice) was added. The resulting mixture was allowed to warm to room temperature and was left at room temperature overnight. To this reaction mixture was added hexanes (30 mL), and the mixture was filtered. The solid was added to a mixture of water:methylene chloride (20 mL:20 mL), cooled to about 0° C., and acidified to pH 1 with concentrated hydrochloric acid. The organic layer was separated, and aqueous layer was extracted with diethyl ether (3×25 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure to about 10 mL. A white solid precipitated and this solid was isolated by filtration to afford the title compound of Step B (1.62 g) as a solid melting at 236-238° C. 1H NMR (Me2SO-d6): δ2.17 (s,3H), 2.68 (m,2H), 2.81 (s,3H), 3.11 (m,2H), 3.50-3.70 (4H), 7.33 (s,1H), 12.78 (s,1H).

Workup

  1. temperaturewhile maintaining the temperature below -60° C
  2. waitwas left at room temperature overnight
  3. filtrationthe mixture was filtered
  4. additionThe solid was added to a mixture of water
  5. temperaturemethylene chloride (20 mL:20 mL), cooled to about 0° C.
  6. customThe organic layer was separated
  7. extractionaqueous layer was extracted with diethyl ether (3×25 mL)
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure to about 10 mL
  11. customA white solid precipitated
  12. customthis solid was isolated by filtration

Sources & evidence

ORD record
ord-e517c4377b744523819979c038ed03df
Source dataset
uspto-grants-1999_09
Patent number
US05952266

Reaction notes

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