Ammonium Chloride → HCID 68838918, compound

HRID 660705

Reaction equation

HRID 660705 reaction equation
[C:1]1([C:7](=[O:16])[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:27]([O:34][C:35]1[CH:40]=[C:39]([CH2:41]Br)[CH:38]=[CH:37][C:36]=1[N+:43]([O-:45])=[O:44])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[CH2:9]([CH:8]([CH2:41][C:39]1[CH:38]=[CH:37][C:36]([N+:43]([O-:45])=[O:44])=[C:35]([O:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:40]=1)[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 64802DihydrochalconeHCID 2733832Lithium HexamethyldisilazideHCID 621150422-Benzyloxy-4-bromomethyl-1-nitrobenzene

Product 1

HCID 68838918HCID 68838918, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1,3 diphenylpropan-1-one (231 mg, 1.1 mmol) in THF (2.5 mL) at −78° C. is added dropwise LiHMDS (1M in THF, 1.3 mL), over a period of 15 min. The mixture is stirred at −78° C. for 30 min then a solution of 2-benzyloxy-4-bromomethyl-1-nitrobenzene (321 mg, 1 mmol) in THF (2.5 mL) is added over a period of 15 min. The mixture is stirred at −78° C. for 15 min, then allowed to slowly warm to RT and stirred there for 45 min. The mixture is diluted with EtOAc, cooled to −25° C. and a solution of saturated ammonium chloride is added dropwise. The organic phase is washed with saturated ammonium chloride and brine, dried over MgSO4, filtered and concentrated to afford crude product which is purified using flash chromatography to give the title compound as a gum.

Workup

  1. stirringThe mixture is stirred at −78° C. for 15 min
  2. temperatureto slowly warm to RT
  3. stirringstirred there for 45 min
  4. temperaturecooled to −25° C.
  5. washThe organic phase is washed with saturated ammonium chloride and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford crude product which
  10. customis purified

Sources & evidence

ORD record
ord-e10ddec916b449c189cda98ce9fb9451
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Linked notes

Loading…