Carbon Dioxide → HCID 18349835, compound

HRID 2268214Notes

Reaction equation

HRID 2268214 reaction equation
[CH3:1][C:2]1([CH3:16])[CH:11](C#C)[CH2:10][C:9]([CH3:15])([CH3:14])[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[CH2:17]([Li])[CH2:18]CC.[C:22](=[O:24])=[O:23].[Cl-].[NH4+]>C1COCC1>[CH3:16][C:2]1([CH3:1])[CH2:11][CH2:10][C:9]([CH3:15])([CH3:14])[C:8]2[CH:7]=[C:6]([C:17]#[C:18][C:22]([OH:24])=[O:23])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 18349828HCID 18349828, compoundHCID 178418339Butyllithium

Product 1

HCID 18349835HCID 18349835, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.1 g (19 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-6-ethynylnaphthalene in 75 ml of THF is introduced into a three-necked flask under a stream of nitrogen, 13.3 ml (21 mmol) of n-butyllithium (2.5M) are added dropwise at −78° C. and the mixture is allowed to return to room temperature. At −78° C., a stream of CO2 is introduced for 30 min and the mixture is allowed to return to room temperature. The reaction medium is poured into saturated ammonium chloride solution and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is triturated with hexane, filtered off and dried. 3.5 g (73%) of the expected propargylic acid, with a melting point of 175-7° C., are collected.

Workup

  1. additionare added dropwise at −78° C.
  2. customto return to room temperature
  3. customto return to room temperature
  4. extractionextracted with ethyl ether
  5. customthe organic phase is separated out after settling
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue obtained
  9. customis triturated with hexane
  10. filtrationfiltered off
  11. customdried
  12. custom3.5 g (73%) of the expected propargylic acid, with a melting point of 175-7° C., are collected

Sources & evidence

ORD record
ord-9eb0bf76c89848adad9fe557be51d638
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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