Tetrahydro-4H-pyran-4-one → HCID 90414228, compound

HRID 1521970Notes

Reaction equation

HRID 1521970 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:15]=[CH:16][C:9]=23)[CH:7]=1.[CH2:28]([Li])CCC.[O:33]1[CH2:38][CH2:37][C:36](=[O:39])[CH2:35][CH2:34]1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([S:17]([C:20]4[CH:25]=[CH:24][C:23]([CH3:28])=[CH:22][CH:21]=4)(=[O:19])=[O:18])[C:15]([C:36]4([OH:39])[CH2:37][CH2:38][O:33][CH2:34][CH2:35]4)=[CH:16][C:9]=23)[CH:7]=1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 90411876HCID 90411876, compoundHCID 178418339Butyllithium

Product 1

HCID 90414228HCID 90414228, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 87A (200 mg, 0.504 mmol) in tetrahydrofuran (5 mL) at −78° C. was added 1.6M n-butyllithium in hexanes (0.473 mL, 0.757 mmol) under nitrogen. The mixture was stirred for 5 minutes and dihydro-2H-pyran-4(3H)-one (101 mg, 1.009 mmol) was added. Stirring was continued at −78° C. for 1 hour and the mixture was warmed to room temperature overnight. The mixture was quenched with water, extracted with ethyl acetate, dried over magnesium sulfate, filtered and purified by flash chromatography (silica gel, 20-100% ethyl acetate/heptanes to afford the title compound. MS (ESI+) m/z 497.0 (M+H)+.

Workup

  1. stirringStirring
  2. waitwas continued at −78° C. for 1 hour
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. custompurified by flash chromatography (silica gel, 20-100% ethyl acetate/heptanes

Sources & evidence

ORD record
ord-05a7becc71794e3f9d9fb827a76027f1
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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