Ammonium Chloride → HCID 9948247, compound

HRID 1422156Notes

Reaction equation

HRID 1422156 reaction equation
[O:1]1[C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=O)=[CH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2.C[Si](N[Si](C)(C)C)(C)C.[Li].[CH2:28]([Mg]Br)[CH:29]=[CH2:30].[Cl-:33].[NH4+:34]>O1CCCC1.CCCCCC>[ClH:33].[O:1]1[C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]([CH2:28][CH:29]=[CH2:30])[NH2:34])=[CH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 18357511HCID 18357511, compoundHCID 57426343Lithium bis(trimethylsilyl)amideHCID 178455850HCID 178455850, compound

Product 1

HCID 9948247HCID 9948247, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3.0 g of 2-(benzo[b]furan-2-yl)-benzaldehyde in 60 ml of tetrahydrofuran, cooled at 0° C. under a nitrogen atmosphere, was added 16.2 ml of a 1 M solution of lithium bis(trimethylsilyl)amine in hexane. After stirring at 0° C. for 20 min 16.2 ml of a 1 M solution of allylmagnesium bromide in tetrahydrofuran was added and the resulting solution stirred at 0° C. for 40 min, then allowed to warm to room temperature over 1 h. Saturated aqueous ammonium chloride was added and the mixture was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and evaporated to dryness under reduced pressure to give a brown oil. The compound was purified by chromatography on silica gel, eluting with 5% methanol in dichloromethane. The pure compound was dissolved in methanol and converted to its hydrochloride salt by addition of a solution of hydrogen chloride in methanol and crystallisation was initiated by addition of diethyl ether. The crystallised salt was filtered affording 2.4 g of 2-(benzo[b]furan-2-yl)-a-2-propenyl-benzenemethanamine hydrochloride, melting at 225-227° C.

Workup

  1. additionwas added
  2. temperatureto warm to room temperature over 1 h
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customto give a brown oil
  7. customThe compound was purified by chromatography on silica gel
  8. washeluting with 5% methanol in dichloromethane
  9. dissolutionThe pure compound was dissolved in methanol
  10. additionconverted to its hydrochloride salt by addition of a solution of hydrogen chloride in methanol and crystallisation
  11. additionwas initiated by addition of diethyl ether
  12. filtrationThe crystallised salt was filtered

Sources & evidence

ORD record
ord-becb218123984eddac39d2c437da9b6b
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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