Ethyl Acetate → Methyl 4-[5-(1-hydroxyallyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 330197Notes

Reaction equation

HRID 330197 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[CH:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][CH2:17][CH3:18])[CH:11]=[C:10]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[O:30][CH3:31])=[O:6].[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1>[OH:6][CH:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][CH2:17][CH3:18])[CH:11]=[C:10]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[O:30][CH3:31])[CH:1]=[CH2:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 14882683Methyl 4-(5-formyl-1-propylindol-3-ylmethyl)-3-methoxybenzoateHCID 178418507HCID 178418507, compound

Product 1

HCID 19870651Methyl 4-[5-(1-hydroxyallyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Vinyl magnesium bromide (3.05 ml of a 1 molar solution in tetrahydrofuran) was added dropwise to a stirred solution of methyl 4-(5-formyl-1-propylindol-3-ylmethyl)-3-methoxybenzoate (1 g, prepared as described in Example 61, part a) in dry tetrahydrofuran (50 ml), at 0° under an atmosphere of nitrogen. The mixture was stirred at 0° for 15 min, and then poured rapidly into a stirred mixture of saturated aqueous ammonium chloride (100 ml) and ethyl acetate (150 ml). The aqueous layer was further extracted with ethyl acetate (75 ml), and the combined organic layers washed (water (twice), brine), dried (MgSO4) and evaporated to give methyl 4-[5-(1-hydroxyallyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (1.03 g, 95%) as a yellow oil; partial NMR (250 MHz, DMSO-d6): 0.80(t, 3H, CH2CH3), 1.75(m, 2H, CH2CH3), 3.83(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.0(m, 4H, ArCH2Ar', NCH2), 5.0-5.3(m, 4H, H2C=CH, CH(OH)), 5.9(m, 1H, CH=CH2).

Workup

  1. customprepared
  2. customat 0°
  3. extractionThe aqueous layer was further extracted with ethyl acetate (75 ml)
  4. washthe combined organic layers washed (water (twice), brine),
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-af1985fc95fa4c479940fa435ec691c9
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

Loading…