4-Fluoroaniline → HCID 68154069, compound

HRID 73621Notes

Reaction equation

HRID 73621 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C[Al](C)C.[O:13]1[C:23]23[C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22]2)[O:17][CH2:16][CH2:15][C@H:14]13.[OH-].[Na+]>C(Cl)Cl.O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C@H:14]2[C@:23]3([OH:13])[C@H:18]([CH2:19][CH2:20][CH2:21][CH2:22]3)[O:17][CH2:16][CH2:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 97314-FluoroanilineHCID 14798Sodium HydroxideHCID 16682925TrimethylaluminumHCID 86668655HCID 86668655, compound

Product 1

HCID 68154069HCID 68154069, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-Fluoroaniline (0.173 g, 1.56 mmol) in CH2Cl2 (3 mL) at 0° C. was added trimethylaluminum (2M in toluene, 0.778 mL) dropwise. The mixture was warmed to rt and stirred for 30 min. Trans hexahydro-1aH,4aH-oxireno[d]chromene (0.200 g, 1.30 mmol) in CH2Cl2 (2 mL) was then added and the mixture was stirred at rt overnight. The reaction was cooled to 0° C. and treated with 50% NaOH (1 mL) then water (1 mL). The reaction mixture was extracted 3× with CH2Cl2. The combined organics were dried, filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 6.90 (t, 2H, J=8.8 Hz), 6.60 (dd, 2H, J=4.2 Hz, 8.8 Hz), 3.88 (dd, 1H, J=5.4 Hz, 12.0 Hz), 3.68-3.74 (m, 1H), 3.47 (dd, 1H, J=4.8 Hz, 11.5 Hz), 3.40 (t, 1H, J=3.2 Hz), 2.30-2.40 (m, 1H), 1.69-1.78 (m, 2H), 1.54-1.68 (m, 5H), 1.45-1.48 (m, 1H), 1.20-1.30 (m, 1H), HRMS (ES) m/z M+H calc'd.: 266.1551. found: 266.1556

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. temperatureThe reaction was cooled to 0° C.
  3. extractionThe reaction mixture was extracted 3× with CH2Cl2
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3aba837bfb3144268684518d12e5d329
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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