Tetrahydrofuran → HCID 11102423, compound

HRID 1596044Notes

Reaction equation

HRID 1596044 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]=3[C:29]([O:31]C)=[O:30])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1COCC1.O[Li].O>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]=3[C:29]([OH:31])=[O:30])(=[O:15])=[O:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 10950695HCID 10950695, compound

Product 1

HCID 11102423HCID 11102423, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of Example 8A (0.12 g, 0.26 mmoL) in MeOH (3 mL), H2O (3 mL), and THF (15 mL) was added LiOH.H2O (0.17 g, 3.84 mmoL). The mixture was stirred at 80° C. for 16 hours, poured into H2O, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated. Purification on silica gel with 2% MeOH/CH2Cl2 provided 0.02 g (20%) of the desired compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on silica gel with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-15197c0b39244443a21cff8d89b1fd64
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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