Tetrahydrofuran → 3,3-Dimethyl-7-hexyl-2,3-dihydro-benzofuran-5-boronic acid

HRID 2085590Notes

Reaction equation

HRID 2085590 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.O1CCCC1.C([Li])(C)(C)C.[B:29](OC)([O:32]C)[O:30]C>CCCCC>[CH3:10][C:7]1([CH3:11])[C:6]2[CH:12]=[C:2]([B:29]([OH:32])[OH:30])[CH:3]=[C:4]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]=2[O:9][CH2:8]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8470Trimethyl borateHCID 227312865-Bromo-3,3-dimethyl-7-hexyl-2,3-dihydro-benzofuran2×HCID 178418306HCID 178418306, compound

Product 1

HCID 227313393,3-Dimethyl-7-hexyl-2,3-dihydro-benzofuran-5-boronic acid

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Following General Procedure A and using 5-bromo-7-hexyl-3,3-dimethyl-2,3-dihydro-benzofuran (Intermediate 53, 1.32 g, 4.26 mmol), anhydrous tetrahydrofuran, 1.7M solution of t-butyllithium in n-pentane and trimethyl borate, the title compound was obtained as a foam that was used as such for the next step without purification and characterization.

Sources & evidence

ORD record
ord-af32fb3b83e6458a91c9eadca3b0296f
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

Loading…