Acetone → HCID 10428233, compound

HRID 239071Notes

Reaction equation

HRID 239071 reaction equation
[OH:1][CH2:2][C:3]([CH3:30])([CH3:29])[CH2:4][C:5]1[CH:6]=[C:7]([C:11]2([C:17]3[CH:18]=[C:19]([CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26])[CH:20]=[CH:21][CH:22]=3)SCCCS2)[CH:8]=[CH:9][CH:10]=1.CC(C)=[O:33]>CN(C=O)C.[Cu]=O.[Cu](Cl)Cl>[OH:1][CH2:2][C:3]([CH3:30])([CH3:29])[CH2:4][C:5]1[CH:6]=[C:7]([C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26])[CH:18]=2)=[O:33])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 180Acetone2×HCID 114649623-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-ol

Product 1

HCID 10428233HCID 10428233, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 24014Cupric ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of copper(II) oxide (0.96 g, 12.1 mmol) and anhydrous copper(II) chloride (3.2 g, 23.8 mmol) in acetone (80 mL) was heated to reflux. A solution of 230 (4.44 g, 10.0 mmol) in acetone (20 mL) and DMF (1.2 mL) was added dropwise over 5 min. After 90 min at reflux temperature, the reaction mixture was cooled to room temperature and filtered. The insoluble material was washed with CH2Cl2 (3×20 mL). The combined organic solutions were washed with aqueous 2 N Na2CO3 solution (50 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel; hexanes/acetone=80/20) to give 232 (2.5 g, 71%) as an oil. 1H NMR (CDCl3): δ 7.68-7.30 (m, 8 H), 3.31 (s, 4 H), 3.03 (s br., 2 H), 2.65 (s, 4 H), 0.88 (s; 12 H). 13C NMR (CDCl3=77.00 ppm): δ 197.42, 139.06, 136.96, 134.60, 131.88, 127.78, 127.55, 70.39, 44.07, 36.30, 23.80. HRMS nba): Calcd for C23 H31O3 (MH+): 355.2273, found: 355.2263. HPLC: 94.5% pure.

Workup

  1. temperaturewas heated to reflux
  2. temperatureAfter 90 min at reflux temperature
  3. filtrationfiltered
  4. washThe insoluble material was washed with CH2Cl2 (3×20 mL)
  5. washThe combined organic solutions were washed with aqueous 2 N Na2CO3 solution (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel; hexanes/acetone=80/20)

Sources & evidence

ORD record
ord-93949882793a4f909b7de5348683a9b6
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

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