Carbon Dioxide → HCID 58066348, compound

HRID 2410566Notes

Reaction equation

HRID 2410566 reaction equation
C([Li])(C)(C)C.CCCCC.[CH3:11][O:12][CH:13]([C:15]1[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])[CH3:14].[C:29](=[O:31])=[O:30]>CCOCC>[CH3:11][O:12][CH:13]([C:15]1[CH:20]=[C:19]([C:29]([OH:31])=[O:30])[CH:18]=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])[CH3:14]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8003PentaneHCID 66678440HCID 66678440, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 58066348HCID 58066348, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of tert-butyllithium in pentane (1.5M, 8.05 mL, 12.1 mmol) was added into anhydrous Et2O (40 mL) cooled at −78° C. under nitrogen atmosphere. Then a solution of 1-(4-bromo-2′-methylbiphenyl-2-yl)ethyl methyl ether (1.84 g, 6.03 mmol) in anhydrous Et2O (10 mL) was added dropwise over 10 minutes. The resulting mixture was stirred at −78° C. for 25 minutes, and then a large excess of dry ice was added and the cooling bath was removed. The reaction mixture was stirred until the temperature came back at RT, then diluted with water (20 ml) and a 5N aqueous solution of NaOH (0.5 mL). The layers were separated and the aqueous layer was washed with Et2O (20 ml). The organic layers were extracted with a 0.1N aqueous solution of NaOH (20 mL). The combined aqueous layers were acidified with a 5N aqueous solution of HCl (until pH˜1) and extracted with MTBE (2×50 mL). The organic layers were washed with brine (30 mL), combined, dried (Na2SO4) and concentrated under vacuum to give a pale yellow solid. After crystallization from a mixture of Et2O and heptane, the title compound was obtained as a white powder. HPLC (Method A) Rt 4.2 min (Purity: 98.2%). LC/MS (Method B): 269.1 (M−H)−. 1H NMR (DMSO-d6, 300 MHz) δ 13.03 (s, 1H), 8.09 (d, J=1.8 Hz, 0.4H), 8.07 (d, J=1.8 Hz, 0.6H), 7.89 (dd, J=7.9, 1.8 Hz, 1H), 7.36-7.24 (m, 3H), 7.22 (d, J=7.9 Hz, 0.4H), 7.20 (d, J=7.9 Hz, 0.6H), 7.13 (d, J=6.9 Hz, 0.4H), 7.07 (d, J=6.9 Hz, 0.6H), 4.12 (q, J=6.4 Hz, 0.4H), 3.92 (q, J=6.4 Hz, 0.6H), 3.05 (s, 1.2H), 3.04 (s, 1.8H), 2.03 (s, 1.8H), 1.98 (s, 1.2H), 1.19 (d, J=6.4 Hz, 1.8H), 1.13 (d, J=6.4 Hz, 1.2H).

Workup

  1. customthe cooling bath was removed
  2. stirringThe reaction mixture was stirred until the temperature
  3. customcame back at RT
  4. additiondiluted with water (20 ml)
  5. customThe layers were separated
  6. washthe aqueous layer was washed with Et2O (20 ml)
  7. extractionThe organic layers were extracted with a 0.1N aqueous solution of NaOH (20 mL)
  8. extractionextracted with MTBE (2×50 mL)
  9. washThe organic layers were washed with brine (30 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated under vacuum
  12. customto give a pale yellow solid
  13. customAfter crystallization
  14. additionfrom a mixture of Et2O and heptane

Sources & evidence

ORD record
ord-1db9349ddb0d4766a59879b52680fd1c
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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