3-Methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid → 3-[4-hydroxy-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]acrylic Acid

HRID 988052Notes

Reaction equation

HRID 988052 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][CH2:18][O:19][C:20]1[C:21](B(O)O)=[CH:22][C:23]2[C:24]([CH3:33])([CH3:32])[CH2:25][CH2:26][C:27]([CH3:31])([CH3:30])[C:28]=2[CH:29]=1>>[OH:8][C:7]1[CH:6]=[CH:5][C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[CH:3][C:2]=1[C:21]1[C:20]([O:19][CH2:18][O:17][CH3:16])=[CH:29][C:28]2[C:27]([CH3:31])([CH3:30])[CH2:26][CH2:25][C:24]([CH3:33])([CH3:32])[C:23]=2[CH:22]=1

Participants

3

Reactant 2

HCID 223453843-Methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylboronic acidHCID 69793988Ethyl 3-(3-bromo-4-hydroxyphenyl)acrylate

Product 1

HCID 697927173-[4-hydroxy-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]acrylic AcidYield 9.9%

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 1.6 g (5.5 mmol) of 3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid obtained in Example 13(b), 150 mg (9%) of the expected compound were obtained in the form of a white solid having a melting point of 101°-103° C.

Sources & evidence

ORD record
ord-aebecf683ca84f0988022a0e90562755
Source dataset
uspto-grants-2003_10
Patent number
US06632963B1

Reaction notes

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