tert-Butyl methyl ether → HCID 42598638, compound

HRID 1755600Notes

Reaction equation

HRID 1755600 reaction equation
[OH:1][C:2]1[C:3]([CH3:23])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])([CH3:14])[CH2:6][CH2:5]2.CC([O:28]C)(C)C>O>[OH:28][C:7]([CH3:14])([C:15](=[O:16])[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:6][CH2:5][C:4]1[C:9](=[O:8])[C:10]([CH3:13])=[C:11]([CH3:12])[C:2](=[O:1])[C:3]=1[CH3:23]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl ether2×HCID 15024205HCID 15024205, compound

Product 1

HCID 42598638HCID 42598638, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 319 mg of (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)(piperidin-1-yl)methanone (1.02 mmol) in 5 mL MTBE which was treated with 1.077 g FeCl3.6H2O in 6 mL H2O. The reaction mixture rapidly turned black which faded to a yellow color over the course of the reaction. An additional 2 mL MTBE was added and stirred vigorously for 3 h at room temp. The reaction was quenched with 10 mL H2O and 10 mL MTBE, the layers separated and the organics washed with H2O until colorless. The combined aqueous phases were extracted 2×10 mL MTBE and the combined organics washed with saturated NaCl and dried over Na2SO4. Flash chromatography yielded 335 mg of 2-(3-hydroxy-3-methyl-4-oxo-4-(piperidin-1-yl)butyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione as a dark yellow oil.

Workup

  1. customThe reaction mixture rapidly turned black which faded to a yellow color over the course of the reaction
  2. customThe reaction was quenched with 10 mL H2O and 10 mL MTBE
  3. customthe layers separated
  4. washthe organics washed with H2O until colorless
  5. extractionThe combined aqueous phases were extracted 2×10 mL MTBE
  6. washthe combined organics washed with saturated NaCl
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-4dfa588dc89640ab8c103126e049ae6c
Source dataset
uspto-grants-2015_10
Patent number
US09169196B2

Reaction notes

Loading…