Ammonium Chloride → HCID 23031153, compound

HRID 1766677Notes

Reaction equation

HRID 1766677 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[CH:17]=[C:16]([CH3:18])[C:15](I)=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])(C)(C)C.[CH2:32]([O:39][C:40]1[CH:47]=[CH:46][C:43]([CH:44]=[O:45])=[CH:42][C:41]=1[CH:48]([CH3:50])[CH3:49])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Cl-].[NH4+]>O1CCCC1.CCCCC>[CH2:32]([O:39][C:40]1[CH:47]=[CH:46][C:43]([CH:44]([C:15]2[C:16]([CH3:18])=[CH:17][C:9]([N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:10]3[C:14]=2[CH2:13][CH2:12][CH2:11]3)[OH:45])=[CH:42][C:41]=1[CH:48]([CH3:50])[CH3:49])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 21110614HCID 21110614, compoundHCID 230311884-(Benzyloxy)-3-(propan-2-yl)benzaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 23031153HCID 23031153, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of dibenzyl(7-iodo-6-methylindan-4-yl) amine (583 mg) in dry tetrahydrofuran (10 mL) was added a 1.48 mol/L solution of tert-butyllithium in n-pentane (1.30 mL) at −100° C. The mixture was stirred for 15 min. Adding dropwise 4-benzyloxy-3-isopropylbenzaldehyde (320 mg) in tetrahydrofuran (5 mL), the reaction mixture turned orange solution. The reaction mixture was stirred at ambient temperature for 15 min, and then warmed to room temperature. To the reaction mixture was added a saturated aqueous solution of ammonium chloride to quench the reaction. Adding brine, the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=3/1−1/1) to give the title compound (497 mg).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 15 min
  2. customto quench
  3. customthe reaction
  4. extractionAdding brine, the mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=3/1−1/1)

Sources & evidence

ORD record
ord-da847fc9fc4e4eb8bb105871fb828266
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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