Hydrochloric Acid → HCID 23031175, compound

HRID 1766674Notes

Reaction equation

HRID 1766674 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15](O)([CH3:17])[CH3:16])=[C:13]([O:19][CH3:20])[C:12]([O:21][C:22]2[C:30]([CH3:31])=[CH:29][C:28]([N:32]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[C:27]3[C:23]=2[CH2:24][CH2:25][CH2:26]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>ClCCl>[CH2:33]([N:32]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:28]1[CH:29]=[C:30]([CH3:31])[C:22]([O:21][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:14]([C:15]([CH3:17])=[CH2:16])[C:13]=2[O:19][CH3:20])=[C:23]2[C:27]=1[CH2:26][CH2:25][CH2:24]2)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21110565HCID 21110565, compound

Product 1

HCID 23031175HCID 23031175, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[6-Benzyloxy-3-(7-dibenzylamino-5-methylindan-4-yloxy)-2-methoxyphenyl]-propane-2-ol (13.9 g) was dissolved in dichloromethane (100 mL). Adding concentrated hydrochloric acid (40 mL), the mixture was stirred for 20 min vigorously. The organic layer was separated, and the water layer was extracted with dichloromethane. The combined organic layers were washed with a 2 mol/L aqueous solution of sodium hydroxide and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1−3/1) to give the title compound (7.97 g).

Workup

  1. customThe organic layer was separated
  2. extractionthe water layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with a 2 mol/L aqueous solution of sodium hydroxide and brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1−3/1)

Sources & evidence

ORD record
ord-ec5a81e4f88e4e5d9fd226dd2700cbc3
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

Loading…