Acetonitrile tetrahydrofuran → HCID 44123688, compound

HRID 1846983Notes

Reaction equation

HRID 1846983 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:6]([CH3:14])=[C:7]([OH:13])[C:8]=2[CH3:12])[O:3]1.C1C[O:29]CC1.C(#N)C>CCOC(C)=O>[OH:29][C:2]([CH3:25])([CH3:1])[CH2:11][CH2:10][C:9]1[C:4](=[O:3])[C:5]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=2)=[C:6]([CH3:14])[C:7](=[O:13])[C:8]=1[CH3:12]

Participants

4

Reactant 2

HCID 22177404Acetonitrile tetrahydrofuranHCID 66919969HCID 66919969, compound

Product 1

HCID 44123688HCID 44123688, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The purified residue containing 2,2,5,7-tetramethyl-8-(4-(trifluoromethyl)phenyl) chroman-6-ol from the above reaction (60 mg) was dissolved in THF/acetonitrile (1:1, 2 ml) and cooled in an ice-water bath. To the resulting solution was added dropwise an aqueous solution of ceric ammonium nitrate (170 mg, 310 μmol in 1 mL) until a reddish color persisted. When the titration endpoint was reached, the mixture was diluted in 5 mL EtOAc, washed once with brine (2 mL). The remaining organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel column chromatography (5→25% EtOAc/hexanes) producing 80 mg of 2-(3-hydroxy-3-methylbutyl)-3,5-dimethyl-6-(4-(trifluoromethyl)phenyl)cyclohexa-2,5-diene-1,4-dione, a yellow oil. 1H NMR (CDCl3, 400 MHz) 7.67 (d, 2H), 7.26 (d, 2H), 2.60 (m, 2H), 2.11 (s, 3H), 1.92 (s, 3H), 1.54 (m, 2H), 1.25 (s, 6H) ppm.

Workup

  1. customfrom the above reaction (60 mg)
  2. temperaturecooled in an ice-water bath
  3. washwashed once with brine (2 mL)
  4. dry with materialThe remaining organics were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel column chromatography (5→25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e3f0cdfb8b9b41e7bf860522d0b8121b
Source dataset
uspto-grants-2015_02
Patent number
US08952071B2

Reaction notes

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