Triethylamine → HCID 23087398, compound

HRID 1950606Notes

Reaction equation

HRID 1950606 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:21])[C:6]2[CH2:7][CH:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:9][CH2:10][C:11]=2[CH:12]=1.[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([O:21][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[C:11]3[C:6]=2[CH2:7][CH:8]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH2:9][CH2:10]3)=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343144-Benzyloxy-phenylboronic acidHCID 11266092HCID 11266092, compound

Product 1

HCID 23087398HCID 23087398, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was synthesized by referring to Tetrahedron Lett., 1998, (19), 2937-2940. To a solution of 3-methoxy-7-(4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-1-ol (853 mg) and 4-benzyloxyphenylboronic acid (1.4 g) in dichloromethane (30 ml) were sequentially added copper(II) acetate (545 mg), molecular sieves 4 A and triethylamine (1.5 g), and the solution was stirred for 8 hours and 40 minutes at room temperature. The insoluble material was filtered through celite pad, the filtrate was adsorbed onto silica gel and purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (1.2 g).

Workup

  1. customThe title compound was synthesized
  2. filtrationThe insoluble material was filtered through celite pad
  3. custompurified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-899316e43d8e493887a813f94ab756f9
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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