Magnesium Bromide → HCID 10928895, compound

HRID 2210417Notes

Reaction equation

HRID 2210417 reaction equation
[Br-].[Mg+2].[Br-].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]2[O:16][C:15]3[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:14]=3[C:13]2([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:26][CH:25]=2)O)=[CH:7][CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H][H]>CCOCC.C(OCC)(=O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[O:16][C:15]3[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:14]=3[C:13]=2[C:24]2[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:28][CH:29]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 82241Magnesium BromideHCID 21226445Aluminium lithium hydrideHCID 53638373HCID 53638373, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10928895HCID 10928895, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Magnesium bromide etherate (0.194 g, 0.75 mmol) was dissolved in 20 ml ether in a two-necked flask under oxygen-free nitrogen atmosphere at room temperature. After stirring for 1 hour, 2-(p-chlorophenylmethylene)-3-[p-(2-morpholinoethoxy)phenyl]-6-methoxy- 2,3-dihydrobenzo[b]furan-3-ol (5) (0.247 g, 0.5 mmol) in ether (10 ml) was added dropwise to the mixture. After stirring for 4 hours, LiAlH4 (0.076 g, 2.0 mmol) was added to the above reaction mixture. The reaction mixture was left overnight at room temperature. After stirring overnight, ethyl acetate was added dropwise till hydrogen evolution ceased. The above mixture was washed with water followed by brine (2×20 ml), dried (anhydrous magnesium sulfate) and the solvent was evaporated off to give an oil which was chromatographed on silica. Elution with (chloroform: hexane: triethylamine=1:1:0.2) yielded a white solid of the free base (Rf =0.4). Yield (60%); m.p. 126°-128° C.; 1H-NMR (CDCl3) (δ) 2.60-2.63 (m, 4H, N(CH2CH2)2O (ring)), 2.85 (t, 2H, OCH2CH2N), 3.74-3.77 (m, 4H, N(CH2CH2)2O (ring)), 3.84 (s, 3H, OCH3), 4.11 (CH2 at C-2), 4.17 (t, 2H, OCH2CH2N), 6.84-7.44 (m, 11H, ArH); m/z (%) 479 (10), 491 (35), 100 (100).

Workup

  1. stirringAfter stirring for 4 hours
  2. waitThe reaction mixture was left overnight at room temperature
  3. stirringAfter stirring overnight
  4. washThe above mixture was washed with water
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. customthe solvent was evaporated off
  7. customto give an oil which
  8. customwas chromatographed on silica
  9. washElution with (chloroform: hexane: triethylamine=1:1:0.2)
  10. customyielded a white solid of the free base (Rf =0.4)
  11. customYield (60%)

Sources & evidence

ORD record
ord-c5696bee81694ff68a2e1f4e3665b48d
Source dataset
uspto-grants-1995_10
Patent number
US05459139

Reaction notes

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