Tetrahydrofuran → HCID 67874296, compound

HRID 1588928Notes

Reaction equation

HRID 1588928 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][O:10][C:4]=2[CH:3]=1.[Li]CCCC.O1CCCC1.[CH:21]([N:24]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:25](=[O:34])[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1)([CH3:23])[CH3:22]>C(OCC)C.C1COCC1.C(OCC)C>[CH:35]1([N:24]([CH:21]([CH3:23])[CH3:22])[C:25](=[O:34])[C:26]2[CH:27]=[CH:28][C:29]([CH:30]([OH:31])[C:2]3[CH:7]=[CH:6][C:5]4[O:8][CH2:9][O:10][C:4]=4[CH:3]=3)=[CH:32][CH:33]=2)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 54488742HCID 54488742, compoundHCID 178418339Butyllithium

Product 1

HCID 67874296HCID 67874296, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21868444Ether tetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of 4-bromo-1,2-(methylenedioxy)benzene (1.00 g, 6.0 mmol) in ethyl ether (30 mL) at 0° under an argon atmosphere is added n-BuLi (3.75 mL of 1.6 M solution in hexane). Tetrahydrofuran (10 mL) is added. The reaction mixture is 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) is added rapidly. The reaction is followed by thin layer chromatography until complete. The reaction is quenched at -15° C. by adding water (50 mL) and 1N HCl(20 mL). The reaction is further diluted with water (300 mL) and extracted three times with EtOAc (50 mL portions). The combined extracts are washed twice with saturated NaCl solution and dried (MgSO4). The drying agent is filtered and the filtrate concentrated in vacuo to give the crude product. The crude product is chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents to give the title compound.

Workup

  1. customThe reaction is quenched at -15° C.
  2. additionby adding water (50 mL) and 1N HCl(20 mL)
  3. additionThe reaction is further diluted with water (300 mL)
  4. extractionextracted three times with EtOAc (50 mL portions)
  5. washThe combined extracts are washed twice with saturated NaCl solution
  6. dry with materialdried (MgSO4)
  7. filtrationThe drying agent is filtered
  8. concentrationthe filtrate concentrated in vacuo
  9. customto give the crude product
  10. customThe crude product is chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-f9040b49b3d442c8871f1ec40661e79c
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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