(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid → N-Methyl-4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-2-pyrrolecarboxaldehyde

HRID 1857884Notes

Reaction equation

HRID 1857884 reaction equation
[CH3:1][C:2]1[C:3](B(O)O)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[CH3:19][N:20]1[CH:24]=[C:23](Br)[CH:22]=[C:21]1[CH:26]=[O:27]>>[CH3:19][N:20]1[CH:24]=[C:23]([C:3]2[C:2]([CH3:1])=[CH:11][C:10]3[C:9]([CH3:13])([CH3:12])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:14])[C:5]=3[CH:4]=2)[CH:22]=[C:21]1[CH:26]=[O:27]

Participants

3

Reactant 2

HCID 10037535(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acidHCID 121967014-bromo-1-methyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 22634646N-Methyl-4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-2-pyrrolecarboxaldehydeYield 59.2%

Procedure

In a similar manner to Example 3(b), by reaction of 3 g (12.1 mmol) of 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid with 1.9 g (10.1 mmol) of N-methyl-4-bromo-2-pyrrolecarboxaldehyde, 1.85 g (59%) of the expected product are obtained in the form of a pale yellow oil.

Sources & evidence

ORD record
ord-9274f65021654aedb69ae40f084b58cc
Source dataset
uspto-grants-2000_11
Patent number
US06147255

Reaction notes

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