Carbon Dioxide → HCID 19047189, compound

HRID 1780596Notes

Reaction equation

HRID 1780596 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][S:6][C:5]=2[S:4][CH:3]=1.O1CCCC1.C([Li])CCC.[C:23](=[O:25])=[O:24]>CCCCCC>[CH3:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][S:6][C:5]=2[S:4][C:3]=1[C:23]([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 19047187HCID 19047187, compoundHCID 178418339Butyllithium

Product 1

HCID 19047189HCID 19047189, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-65 °C

Procedure

8.20 g (0.041 mol) of the title compound of Step B was added to 200 mL of tetrahydrofuran under nitrogen. The solution was cooled to about -65° C. and 21 mL (0.053 mol) of 2.5M n-butyllithium was added dropwise while keeping the reaction temperature below -55° C. After stirring for 1 h, an excess of solid CO2 was added in portions and the mixture was allowed to warm to room temperature over 2 hr. The mixture was then diluted with 150 mL of hexane and the precipitate was collected by filtration. The precipitate was added to a mixture of 300 mL of water and 300 mL of methylene chloride, cooled to about 0° C., and then acidified to pH 1 with concentrated hydrochloric acid. The layers were separated and the aqueous layer was extracted with diethyl ether (2×300 mL). The combined organic layers were dried (MgSO4), filtered, and evaporated to dryness to yield 6.36 g of the title compound of Step C as a solid melting at 176°-178° C. 1H NMR (DMSO-d6): δ 1.3 (s,6H), 1.95 (m,2H), 2.6 (s,3H), 3.08 (m,2H), 12.7 (br s, 1H).

Workup

  1. customthe reaction temperature below -55° C
  2. temperatureto warm to room temperature over 2 hr
  3. filtrationthe precipitate was collected by filtration
  4. additionThe precipitate was added to a mixture of 300 mL of water and 300 mL of methylene chloride
  5. temperaturecooled to about 0° C.
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with diethyl ether (2×300 mL)
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-223353be8a2d43699b554e423914e2ff
Source dataset
uspto-grants-1997_05
Patent number
US05631210

Reaction notes

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