Carbon Dioxide → HCID 15617904, compound

HRID 1165017Notes

Reaction equation

HRID 1165017 reaction equation
[C:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[O:18][CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:25](=[O:27])=[O:26]>O1CCCC1>[C:1]1([CH2:7][C:8]2[CH:17]=[C:16]([C:25]([OH:27])=[O:26])[C:15]3[C:10]([C:9]=2[O:18][CH3:19])=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 15617899HCID 15617899, compoundHCID 178418339Butyllithium

Product 1

HCID 15617904HCID 15617904, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound of Example 94 Part B (5.00 g, 0.015 mole) in dry tetrahydrofuran (50 mL) was cooled to -78° and treated dropwise with n-butyllithium (1.55M in hexane; 10.9 mL, 0.017 mole). The mixture was stirred at -78° for 45 minutes, and a stream of gaseous carbon dioxide was directed onto the surface of the stirred solution. The cooling bath was removed from the reaction vessel and the addition of carbon dioxide was continued for 5 minutes. The mixture was then poured into 1.0N hydrochloric acid, and the crude product isolated by extraction with methylene chloride. This was recrystallized (methylcyclohexane) to provide the title compound (4.0 g, 90%) as a pale yellow solid, mp 146°-148°.

Workup

  1. customThe cooling bath was removed from the reaction vessel
  2. additionthe addition of carbon dioxide
  3. waitwas continued for 5 minutes
  4. additionThe mixture was then poured into 1.0N hydrochloric acid
  5. customthe crude product isolated by extraction with methylene chloride
  6. customThis was recrystallized (methylcyclohexane)

Sources & evidence

ORD record
ord-40c04a94f5ab45e080be2dd3ad786ff1
Source dataset
uspto-grants-1990_03
Patent number
US04906636

Reaction notes

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