Ethanol → HCID 46186199, compound

HRID 1851099Notes

Reaction equation

HRID 1851099 reaction equation
[Si]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)(O)[CH:14]([C:19]3[CH:24]=[CH:23][C:22]([O:25][Si](C(C)(C)C)(C)C)=[CH:21][CH:20]=3)[CH2:15][O:16]2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.CC1C=CC(S(O)(=O)=O)=CC=1.C(O)C>CO>[OH:25][C:22]1[CH:21]=[CH:20][C:19]([C:14]2[CH:13]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=3)[O:16][CH:15]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 66630260HCID 66630260, compound

Product 1

HCID 46186199HCID 46186199, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-(tert-Butyldimethylsilyloxy)-3-(4 (tert-butyldimethylsilyloxy)phenyl)-4-(4-methoxyphenyl)chroman-4-ol (42 g), pTsOH (435 g), boiling chips and 2.5 L of ethanol win, combined in a 2-neck SL round bottom flask with condenser attached. The reaction was heated at reflux for 3 hours. The solvent was concentrated in vacuo to ˜1000 ml before being poured into chilled, stirred water (700 ml). The mixture was then extracted with ethyl acetate, the combined organic layers washed with water (3×2 L) brine (1×500 ml), dried over anhydrous magnesium sulphate and filtered and solvent removed in vacuo to give red/brown oil. The oil was dissolved in methanol (˜100 ml) ad put in freezer overnight.

Workup

  1. customcombined in a 2-neck SL round bottom flask with condenser
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 3 hours
  4. concentrationThe solvent was concentrated in vacuo to ˜1000 ml
  5. additionbefore being poured
  6. temperatureinto chilled
  7. extractionThe mixture was then extracted with ethyl acetate
  8. washthe combined organic layers washed with water (3×2 L) brine (1×500 ml)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. filtrationfiltered
  11. customsolvent removed in vacuo
  12. customto give red/brown oil

Sources & evidence

ORD record
ord-17a7433827f440d0a441c54507c46ba1
Source dataset
uspto-grants-2015_02
Patent number
US08957109B2

Reaction notes

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