2-Indanone → HCID 18690300, compound

HRID 1872298Notes

Reaction equation

HRID 1872298 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][C:9]([Mg]Br)=[CH:8][CH:7]=1.[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C:15]1=[O:23]>C1COCC1>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:15]2([OH:23])[CH2:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 119832-Indanone2×HCID 24636Cerium(III) chlorideHCID 178418676HCID 178418676, compound

Product 1

HCID 18690300HCID 18690300, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of anhydrous cerium chloride (43.9 g, 178.0 mmol) in THF (250 mL) was stirred at room temperature for 2 hours under nitrogen. 4-Fluorophenylmagnesium bromide (75.6 mL of 2.0 M solution in diethyl ether, 151.2 mmol) was added at 0° C. and stirred for 3.5 h. A solution of 2-indanone (15.36 g, 116.4 mmol) in THF (20 mL) was added at the same temperature. After stirring at 0° C. for 3 h, the mixture was allowed to warm to room temperature and kept at ambient temperature over-night (12 h). It was then treated with 5% aqueous hydrochloric solution. The solution was extracted with diethyl ether (4*200 mL). All etheral layers were combined, washed with water (100 mL), dried over anhydrous magnesium sulphate and concentrated to give the crude product. Unreacted 2-indanone was distilled off. The residue was subjected to Kugelrohr distillation (165° C./0.3 mm Hg). 2-(4-Fluorophenyl)-2-indanol (21.62 g) was obtained in pure form. 1H-N.M.R. (CDCl3) d 2.22 (br s, 1H), d 3.24 (d, J=16.3 Hz, 2H), d 3.47 (d, J=16.3 Hz, 2H), d 7.04 (m, 2H), d 7.20-7.28(m, 4H), d 7.52(br d, J=9.0, 5.3 Hz, 2H).

Workup

  1. stirringstirred for 3.5 h
  2. stirringAfter stirring at 0° C. for 3 h
  3. temperatureto warm to room temperature
  4. waitkept at ambient temperature over-night
  5. custom(12 h)
  6. extractionThe solution was extracted with diethyl ether (4*200 mL)
  7. washwashed with water (100 mL)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. concentrationconcentrated
  10. customto give the crude product
  11. distillationwas distilled off
  12. distillationThe residue was subjected to Kugelrohr distillation (165° C./0.3 mm Hg)

Sources & evidence

ORD record
ord-6108788097b24f5da131c8e172bc4c2a
Source dataset
uspto-grants-2000_08
Patent number
US06107431

Reaction notes

Loading…