HCID 68875089, compound → HCID 68872386, compound

HRID 2224923Notes

Reaction equation

HRID 2224923 reaction equation
[CH:1]1([CH2:5][C:6]2([CH3:23])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([OH:16])=[C:8](C(OCC)=O)[C:7]2=[O:22])[CH2:4][CH2:3][CH2:2]1>O1CCOCC1.Cl.O>[CH:1]1([CH2:5][C:6]2([CH3:23])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([OH:16])=[CH:8][C:7]2=[O:22])[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 1

HCID 68875089HCID 68875089, compound

Product 1

HCID 68872386HCID 68872386, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 55E (0.055 g, 0.174 mmol) in 4 mL of dioxane and 4 mL of 1N HCl was refluxed for 3 hours. The solution was cooled to room temperature, diluted with water and extracted with 3× ethyl acetate. The combined organic layers were dried over MgSO4, and concentrated in vacuo to yield the title compound (0.035 g, 83% yield) as an oil that solidifies on standing. 1H NMR (300 MHz, DMSO-d6): δ ppm 1.16 m, 3 H) 1.48 (s, 3H) 1.70 m, 3 H) 2.04 m, 2 H) 2.21 m, 1 H) 5.76 m, 1 H) 7.30 m, 1 H) 7.44 (m, 1 H) 7.63 m, 1 H) 8.00 (d, J=8.09 Hz, 1 H). MS (ESI+) m/z=243 (M+H)+.

Workup

  1. extractionextracted with 3× ethyl acetate
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c7053a7b50a4bbd9c6edbbb791e6efe
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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