Ammonium Chloride → HCID 19047579, compound

HRID 742447Notes

Reaction equation

HRID 742447 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12].[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>CCOCC.C1CCCCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:12]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 45474914-methoxy-2,3-dihydro-1H-inden-1-oneHCID 178506676HCID 178506676, compound2×

Product 1

HCID 19047579HCID 19047579, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21895417Cyclohexane diethyletherSolvent

Procedure

To a solution of 9.38 g (0.057 mol) of 4-methoxy-1-indanone in 250 mL of ether cooled to 0° C. was added dropwise over 5 min 33.72 mL (0.0607 mol) of 1.8M phenyllithium in cyclohexane/ether and the mixture was stirred at room temperature for 1 h. An additional (10 mL) phenyllithium solution was added and stirred at room temperature for 1 h. To the reaction mixture was added saturated ammonium chloride solution and the resulting mixture was extracted with ethyl acetate (3×100 mL), and the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford 14.3 g of crude 4-methoxy-1-phenyl-indan-1-ol which was used directly in the next step without further purification.

Workup

  1. stirringstirred at room temperature for 1 h
  2. extractionthe resulting mixture was extracted with ethyl acetate (3×100 mL)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-003e151b46fb44758393c6b6db95be79
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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