Ethyl Acetate → HCID 21107223, compound

HRID 1869901Notes

Reaction equation

HRID 1869901 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2([CH3:13])[CH3:12])=[C:4]([O:14][CH3:15])[CH:3]=1.C(OCC)(=[O:18])C>C(O)(=O)C.O.CCCCCC.[O-2].[O-2].[O-2].[Cr+6]>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[C:4]([O:14][CH3:15])[CH:3]=1)[C:6](=[O:18])[CH2:7][CH2:8][C:9]2([CH3:12])[CH3:13]

Participants

7

Reactant 2

HCID 8857Ethyl AcetateHCID 21107238HCID 21107238, compound2×

Product 1

HCID 21107223HCID 21107223, compoundYield 33%

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 7-bromo-5-methoxy-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalene (Intermediate 63, 5.6 g, 20.81 mmol) in glacial acetic acid (20 mL) was cooled to 0° C. and treated with a solution of chromium trioxide (6.16 g, 61.6 mmol) in acetic acid and water (25 mL). The reaction mixture was then allowed to warm to ambient temperature and stirred for 48 h. It was diluted with water and extracted with diethyl ether (×2). The combined organic phase was washed with water (×3), saturated aqueous sodium bicarbonate (×1) and brine (×1), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford an oil. Flash column chromatography over silica gel (230-400 mesh) using 10-20-100% ethyl acetate in hexane as the eluent afforded the title compound (2 g, 33%) as a yellow oil and recovered starting material (2.2 g, 39%).

Workup

  1. extractionextracted with diethyl ether (×2)
  2. washThe combined organic phase was washed with water (×3), saturated aqueous sodium bicarbonate (×1) and brine (×1)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford an oil

Sources & evidence

ORD record
ord-e1da4dbf2ef04a17b1cd74426a47053a
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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