Tetrahydrofuran → HCID 86760278, compound

HRID 1245149Notes

Reaction equation

HRID 1245149 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH3:17][O:18][C:19]1[C:20]([CH3:33])=[C:21]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH:22]=[O:23].[Cl-].[NH4+].[O:36]1CCCC1>>[CH3:17][O:18][C:19]1[C:20]([CH3:33])=[C:21]([CH:22]([C:12]2[CH:13]=[CH:14][C:9]([O:8][C:1](=[O:36])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[OH:23])[C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5462224MagnesiumHCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehyde

Product 1

HCID 86760278HCID 86760278, compoundYield 92%

Procedure

Under ice-cooling, into a Grignard reagent (30 ml, a tetrahydrofuran solution) prepared from 4-(benzyloxy)bromobenzene (8.00 g, 0.030 mol) and magnesium (0.81 g, 0.033 mol) was dropped a solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (3.65 g, 0.015 mol) in anhydrous tetrahydrofuran (20 ml) and the mixture was stirred for 2 hours more. The reaction solution was poured into a saturated aqueous solution of ammonium chloride followed by extracting with ether. The extract was washed with a saturated saline and dried. The reaction solution was filtered and the crude product obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (5.93 g, 0.014 mol, 92%).

Workup

  1. extractionby extracting with ether
  2. washThe extract was washed with a saturated saline
  3. customdried
  4. filtrationThe reaction solution was filtered
  5. customthe crude product obtained
  6. concentrationby concentrating the filtrate
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-912478771347477a9c656b4c9d1b3469
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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