Triethylamine → 4-(3-Benzyloxy-phenoxy)-2-methoxymethoxy-6-methyl-benzaldehyde

HRID 1798151Notes

Reaction equation

HRID 1798151 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([O:11][CH2:12][O:13][CH3:14])[CH:3]=1.[CH2:15]([O:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCN(CC)CC>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:15]([O:22][C:23]1[CH:28]=[C:27]([CH:26]=[CH:25][CH:24]=1)[O:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([O:11][CH2:12][O:13][CH3:14])[CH:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343133-Benzyloxy-phenylboronic acidHCID 582925684-Hydroxy-2-methoxymethoxy-6-methyl-benzaldehyde

Product 1

HCID 866539784-(3-Benzyloxy-phenoxy)-2-methoxymethoxy-6-methyl-benzaldehydeYield 34%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxy-2-methoxymethoxy-6-methyl-benzaldehyde (5.3 g, 27.2 mmol), 3-benzyloxyphenylboronic acid (9.3 g, 40.8 mmol), Cu(OAc)2 (4.9 g, 27.2 mmol), Et3N (18.9 mL, 135.9 mmol) and 4 Å molecular sieves (26 g) in DCM (150 mL) was stirred at room temperature for 12 hours. The reaction mixture was filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 4-(3-benzyloxy-phenoxy)-2-methoxymethoxy-6-methyl-benzaldehyde (3.5 g, 34%). 1H NMR (400 MHz, CDCl3): δ 10.55 (s, 1H), 7.43-7.25 (m, 6H), 6.82 (dd, J=2.0, 8.4 Hz, 1H), 6.69-6.66 (m, 3H), 6.37 (s, 1H), 5.21 (s, 2H), 5.04 (s, 2H), 3.49 (s, 3H), 2.52 (s, 3H). MS (ESI) m/z=379 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-748f11dba938479c910e3cf27ebf03c8
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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