Methanol → HCID 86601718, compound

HRID 2104294Notes

Reaction equation

HRID 2104294 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])[O:8][CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])([O:19][CH2:20][CH3:21])[CH2:15][CH:14]=1)=O)([CH3:4])([CH3:3])[CH3:2].CO>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([O:8][CH2:9][CH2:10][NH:12][C:13]2[CH:14]=[CH:15][C:16]([N+:22]([O-:24])=[O:23])([O:19][CH2:20][CH3:21])[CH2:17][CH:18]=2)[CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 86601719HCID 86601719, compound2×

Product 1

HCID 86601718HCID 86601718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.92 g (4.5 mmol) of 2-[3,5-di(tert-butyl)-4-hydroxyphenoxy]-N-(4-nitrophenetyl)acetamide (synthesis intermediate of compound 47) is introduced into 80 ml of anhydrous THF in a flask, under an argon atmosphere. A solution of 13.45 ml (13.45 mmol) of BH3 in THF is added to the reaction mixture and the mixture is agitated while heating at reflux for 4 hours 30 minutes. At the end of the reaction, 10 ml of MeOH is added and heating is maintained for a further 30 minutes. The reaction mixture is then concentrated under vacuum, the residue is taken up in 30 ml of a MeOH/HCl 3N mixture (2/1) and the mixture is taken to reflux for another hour. The reaction mixture is returned to 22° C., diluted with 50 ml of CH2Cl2 and 2M aqueous soda is added until a basic pH is obtained. After decantation, the organic phase is washed successively with 20 ml of water and 20 ml of brine, dried over sodium sulphate, filtered and concentrated under vacuum. The expected product is purified by chromatography on a silica column (eluent: CH2Cl2/EtOH: 25/1). Pale yellow solid.

Workup

  1. temperaturewhile heating
  2. temperatureat reflux for 4 hours 30 minutes
  3. additionis added
  4. temperatureheating
  5. temperatureis maintained for a further 30 minutes
  6. concentrationThe reaction mixture is then concentrated under vacuum
  7. temperatureto reflux for another hour
  8. customis returned to 22° C.
  9. additiondiluted with 50 ml of CH2Cl2 and 2M aqueous soda
  10. additionis added until a basic pH
  11. customis obtained
  12. washAfter decantation, the organic phase is washed successively with 20 ml of water and 20 ml of brine
  13. dry with materialdried over sodium sulphate
  14. filtrationfiltered
  15. concentrationconcentrated under vacuum
  16. customThe expected product is purified by chromatography on a silica column (eluent: CH2Cl2/EtOH: 25/1)

Sources & evidence

ORD record
ord-f384f1cf4db14063974bcacbd60ee990
Source dataset
uspto-grants-2009_08
Patent number
US07576241B2

Reaction notes

Loading…