3-(4-Methoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid → 3-{4-hydroxy-3-[3-(4-methoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic Acid

HRID 988049Notes

Reaction equation

HRID 988049 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([O:13]CC)=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[CH3:16][O:17][C:18]1[CH:42]=[CH:41][C:21]([CH2:22][O:23][C:24]2[C:25](B(O)O)=[CH:26][C:27]3[C:28]([CH3:37])([CH3:36])[CH2:29][CH2:30][C:31]([CH3:35])([CH3:34])[C:32]=3[CH:33]=2)=[CH:20][CH:19]=1>>[OH:8][C:7]1[CH:2]=[CH:3][C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[CH:5][C:6]=1[C:25]1[C:24]([O:23][CH2:22][C:21]2[CH:41]=[CH:42][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)=[CH:33][C:32]2[C:31]([CH3:35])([CH3:34])[CH2:30][CH2:29][C:28]([CH3:37])([CH3:36])[C:27]=2[CH:26]=1

Participants

3

Reactant 2

HCID 223454063-(4-Methoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylboronic acidHCID 69793988Ethyl 3-(3-bromo-4-hydroxyphenyl)acrylate

Product 1

HCID 697924543-{4-hydroxy-3-[3-(4-methoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic AcidYield 51.7%

Procedure

In a manner similar to that of Example 1(c), by reaction of 1.0 g (3.7 mmol) of ethyl 3-(3-bromo-4-hydroxyphenyl)acrylate obtained in Example 34(d) with 2.0 g (5.5 mmol) of 3-(4-methoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid obtained above, 930 mg (49%) of the expected compound were obtained in the form of a colorless oil.

Sources & evidence

ORD record
ord-3cba024f681046fc8e6ad2e9aceaf39e
Source dataset
uspto-grants-2003_10
Patent number
US06632963B1

Reaction notes

Loading…