Ammonium Chloride → HCID 21110565, compound

HRID 1766673Notes

Reaction equation

HRID 1766673 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([O:18][CH3:19])[C:12]([O:20][C:21]2[C:29]([CH3:30])=[CH:28][C:27]([N:31]([CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:26]3[C:22]=2[CH2:23][CH2:24][CH2:25]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:46][Li].[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[CH2:1]([O:8][C:9]1[C:14]([C:15]([OH:17])([CH3:46])[CH3:16])=[C:13]([O:18][CH3:19])[C:12]([O:20][C:21]2[C:29]([CH3:30])=[CH:28][C:27]([N:31]([CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[C:26]3[C:22]=2[CH2:23][CH2:24][CH2:25]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21110563HCID 21110563, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 21110565HCID 21110565, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[6-benzyloxy-3-(7-dibenzylamino-5-methylindan-4-yloxy)-2-methoxyphenyl]ethanone (13.3 g) in tetrahydrofuran (100 mL) was added dropwise a 1.14 mol/L solution of methyllithium in diethyl ether (30 mL) under an argon atmosphere at −78° C. The mixture was stirred for 30 min, and then warmed up to room temperature gradually. To the dark-red reaction mixture was added a saturated aqueous solution of ammonium chloride (40 mL). The reaction mixture was stirred for 10 min. The organic solvent was evaporated under reduced pressure to dryness. The residue was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to dryness to give 2-[6-benzyloxy-3-(7-dibenzylamino-5-methylindan-4-yloxy)-2-met hoxyphenyl]-propane-2-ol (13.9 g).

Workup

  1. stirringThe reaction mixture was stirred for 10 min
  2. customThe organic solvent was evaporated under reduced pressure to dryness
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-7a44041e197a4f0b91b9752e105eb4ca
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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