Aluminum(III) Chloride → HCID 72195105, compound

HRID 626298Notes

Reaction equation

HRID 626298 reaction equation
C([O:8][C@@H:9]([C:11]1[O:12][C:13]2[C:18]([C:19](=[O:27])[C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:17][C:16]([F:28])=[CH:15][CH:14]=2)[CH3:10])C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[F:28][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C@H:9]([OH:8])[CH3:10])=[C:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:19]2=[O:27]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 117966950HCID 117966950, compound

Product 1

HCID 72195105HCID 72195105, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (R)-2-(1-(benzyloxy)ethyl)-6-fluoro-3-phenyl-4H-chromen-4-one (0.63 g, 1.68 mmol) in dichloromethane (6 ml) cooled to 0° C., aluminium chloride (0.330 g, 2.52 mmol) was added portion wise and stirred at RT for 6 h. The reaction mixture was quenched with 2N HCl solution, extracted with dichloromethane, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as yellow solid (0.348 g, 73%). 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.83 (m, 1H), 7.76 (m, 2H), 7.46 (m, 3H), 7.30 (m, 2H), 5.60 (d, J=4.9 Hz, 1H), 4.53 (m, 1H), 1.38 (d, J=6.5 Hz, 3H). Mass: 285.2 (M++1). Purity: 86.82%. [α]25D −1.18 (c=1, CHCl3). Enantiomeric excess: 97.8%, enriched in the late eluting isomer (retention time: 11.39 min.) as determined by HPLC on a chiralpak AD-H column.

Workup

  1. customThe reaction mixture was quenched with 2N HCl solution
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-ba0d8b4230b84ab2aa505b35570a9472
Source dataset
uspto-grants-2016_04
Patent number
US09309216B2

Reaction notes

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