Carbon Dioxide → HCID 22612227, compound

HRID 1819924Notes

Reaction equation

HRID 1819924 reaction equation
[OH:1][C:2]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)([CH2:5][CH3:6])[CH2:3][CH3:4].C([Li])CCC.[C:17](=[O:19])=[O:18]>C1COCC1>[OH:1][C:2]([C:7]1[S:8][C:9]([C:17]([OH:19])=[O:18])=[CH:10][CH:11]=1)([CH2:3][CH3:4])[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 57890042HCID 57890042, compoundHCID 178418339Butyllithium

Product 1

HCID 22612227HCID 22612227, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. mixture of 2-(3-hydroxy-3-pentyl)thiophene (0.34 g, 2.0 mmol) in THF (2 ml) is added of 1.6 M n-butyllithium in Hex (2.75 ml, 4.4 mmol). The mixture is allowed to warm to RT and powderized dry ice (CO2) is added. After one h, the mixture is partitioned between diethyl ether and 1N NaHCO3. The aqueous layer is washed with ether, acidified with conc. HCl and extracted with ether. The organic layer is Na2SO4 dried, filtered, and concentrated to give the title compound (0.236 g, 53%).

Workup

  1. customAfter one h, the mixture is partitioned between diethyl ether and 1N NaHCO3
  2. washThe aqueous layer is washed with ether
  3. extractionextracted with ether
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6565799450f24ba48a1e068f160c3f14
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

Loading…