Pentane → HCID 22731304, compound

HRID 2085575Notes

Reaction equation

HRID 2085575 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.C([Li])(C)(C)C.CCCCC.[B:27](OC)([O:30]C)[O:28]C>O1CCCC1>[CH3:10][C:7]1([CH3:11])[C:6]2[CH:12]=[C:2]([B:27]([OH:30])[OH:28])[CH:3]=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=2[O:9][CH2:8]1

Participants

6

Reactant 4

HCID 8003PentaneHCID 8470Trimethyl borateHCID 107793125-Bromo-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furanHCID 178418306HCID 178418306, compound

Product 1

HCID 22731304HCID 22731304, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure A and using 5-bromo-3,3-dimethyl-7-t-butyl-2,3-dihydro-benzofuran (1.42 g, 7 mmol), 15 mL of anhydrous tetrahydrofuran, 1.7M solution of t-butyllithium in n-pentane (8.25 mL, 14 mmol) and trimethyl borate (1.5 mL, 14 mmol), the title compound was obtained as a foam that was used as such for the next step without purification and characterization. 5-Bromo-3,3-dimethyl-7-t-butyl-2,3-dihydro-benzofuran can be prepared as described by Janusz et al. in J. Med. Chem. 1998, 41, 1124-1137.

Sources & evidence

ORD record
ord-e36c684c17e64b5c94c79e0b412e02b4
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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