Tetrahydrofuran → HCID 10089452, compound

HRID 375807Notes

Reaction equation

HRID 375807 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[CH2:9][N:10]([C:11]([O:13][C:14](C)(C)C)=[O:12])[C:4]=2[CH:3]=1.[Li]CCCC.[CH2:29]1[CH2:33][O:32][CH2:31][CH2:30]1>O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[CH:9]3[CH:14]([C:31]4[O:32][CH:33]=[CH:29][CH:30]=4)[O:13][C:11](=[O:12])[N:10]3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14938748HCID 14938748, compoundHCID 178418339Butyllithium

Product 1

HCID 10089452HCID 10089452, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

A stirring solution of 1 (2.0 g, 6.04 mmol) in 40 mL of THF was cooled to -78° C. followed by the addition of n-BuLi (1.6M, 4.32 mL, 6.91 mmol). The mixture was stirred at -78° C. for 30 minutes and treated with furalaldehyde (670 mg, 6.97 mmol) and then slowly warmed to room temperature and diluted with 16 mL of water. The mixture was then extracted with ether (200 mL×2) and the combined extracts were washed with brine (saturated, 50 mL) and dried (Na2SO4). The extracts were concentrated to give the crude product (2.5 g), which was purified by HPLC with 20% EtOAc/heptane to yield Compounds 13, 14a and 14b as follows:

Workup

  1. additiontreated with furalaldehyde (670 mg, 6.97 mmol)
  2. temperatureslowly warmed to room temperature
  3. extractionThe mixture was then extracted with ether (200 mL×2)
  4. washthe combined extracts were washed with brine (saturated, 50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationThe extracts were concentrated
  7. customto give the crude product (2.5 g), which
  8. customwas purified by HPLC with 20% EtOAc/heptane

Sources & evidence

ORD record
ord-53eaa7aed7064b499b5173fed8b68c6d
Source dataset
uspto-grants-1996_01
Patent number
US05488046

Reaction notes

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