Tetrahydrofuran → HCID 19754883, compound

HRID 1588903Notes

Reaction equation

HRID 1588903 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C([Li])CCC.O1CCCC1.[CH:22]([N:25]([CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)[C:26](=[O:35])[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1)([CH3:24])[CH3:23]>C(OCC)C.O1CCCC1.C(OCC)C.C(OCC)(=O)C.CCCCCC>[CH:36]1([N:25]([CH:22]([CH3:24])[CH3:23])[C:26](=[O:35])[C:27]2[CH:28]=[CH:29][C:30]([CH:31]([C:2]3[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=3)[OH:32])=[CH:33][CH:34]=2)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 54488742HCID 54488742, compoundHCID 178418339Butyllithium

Product 1

HCID 19754883HCID 19754883, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 21226206Ethyl acetate hexaneSolventHCID 21868444Ether tetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of 4-bromoveratrole (0.77 ml, 6.0 mmol) in ethyl ether (30 mL) at 0° C. under an argon atmosphere was added n-butyl lithium (3.75 mL of 1.6 M solution in hexane). A white precipitate formed and tetrahydrofuran (THF) (10 mL) was added. The reaction mixture was cooled to -20° C. and a solution of terephthalaldehydic acid N-isopropyl-N-cyclohexyl amide (0.82 g, 3.0 mmol) in THF: ethyl ether (4:3, 35 mL) was added rapidly. Thin layer chromatography (TLC) (50% ethyl acetate/hexane) after 5 min showed the reaction was nearly complete. The reaction was quenched at -15° C. by adding water (50 mL) and 1N HCl(20 mL). The reaction was further diluted with water (300 mL) and extracted three times with ethyl acetate (50 mL portions). The combined extracts were washed twice with saturated NaCl solution and dried (MgSCO4). The drying agent was filtered and the filtrate concentrated in vacuo to give the crude product. The crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents to give the title compound as an amorphous solid.

Workup

  1. customA white precipitate formed
  2. customThe reaction was quenched at -15° C.
  3. additionby adding water (50 mL) and 1N HCl(20 mL)
  4. additionThe reaction was further diluted with water (300 mL)
  5. extractionextracted three times with ethyl acetate (50 mL portions)
  6. washThe combined extracts were washed twice with saturated NaCl solution
  7. dry with materialdried (MgSCO4)
  8. filtrationThe drying agent was filtered
  9. concentrationthe filtrate concentrated in vacuo
  10. customto give the crude product
  11. customThe crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-bea942ca3f874eb28b6bf98c2ccaab4c
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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