Carbon Dioxide → HCID 29003638, compound

HRID 442584Notes

Reaction equation

HRID 442584 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:9]([F:22])[CH:8]=1.[C:23](=[O:25])=[O:24].Cl>C1COCC1>[F:22][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[O:13][C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:23]([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 54354285HCID 54354285, compoundHCID 178418339Butyllithium

Product 1

HCID 29003638HCID 29003638, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of n-butyllithium (2.5M, 17.2 ml, 0.043 mol) in hexanes was added, dropwise, to a cooled (-78° C.), stirred solution of compound 35 (10.00 g, 0.033 mol) in dry THF (100 ml) under a dry nitrogen atmosphere and left to stir for 20 min. The resultant solution was poured into a slush of solid carbon dioxide and dry THF. This was left overnight at room temperature and then acidified with dilute hydrochloric acid. The TBF/water azeotrope was evaporated off in vacuo and the residue was dissolved in diethyl ether, washed with water and then extracted with 5% sodium hydroxide solution which was acidified with dilute hydrochloric acid. The product was extracted with diethyl ether and the ethereal solution was washed with water until acid-free, dried (MgSO4) and evaporated in vacuo to leave an off-white, semi-solid.

Workup

  1. waitleft
  2. waitThis was left overnight at room temperature
  3. customThe TBF/water azeotrope was evaporated off in vacuo
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washwashed with water
  6. extractionextracted with 5% sodium hydroxide solution which
  7. extractionThe product was extracted with diethyl ether
  8. washthe ethereal solution was washed with water until acid-free,
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo
  11. customto leave an off-white, semi-solid

Sources & evidence

ORD record
ord-2d6617dd6280432591b02dd946f89289
Source dataset
uspto-grants-1999_04
Patent number
US05891358

Reaction notes

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