Lithium tri-s-butylborohydride → 5-Bromo-1-methoxy-3-methyl-8-(1-methylethoxy)naphthalene

HRID 742102Notes

Reaction equation

HRID 742102 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[C:9]([CH2:12]Br)[CH:10]=2)[C:5]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>ClCCl>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[C:9]([CH3:12])[CH:10]=2)[C:5]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydride2×HCID 15341856HCID 15341856, compound

Product 1

HCID 110559695-Bromo-1-methoxy-3-methyl-8-(1-methylethoxy)naphthaleneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. cold solution of 7.60 g (19.6 mmol) 1-bromo-7-bromomethyl-4-isopropoxy-5-methoxy-naphthalene in 150 mL dry dichloromethane, 20.0 mL (20.0 mmol) of a 1M L-selectride-solution was added under Ar. After 2 h, further 2.50 mL (2.50 mmol) 1M L-selectride-solution was added. After that the solvent was removed in vacuo and the residue was filtered over a short silica gel column (petroleum/acetone, 30:1). After removal of the solvent in vacuo, the residue was recrystallized from acetone to give 5.90 g (98%) of 4 as colorless needles (m.p. 78° C.).

Workup

  1. customAfter that the solvent was removed in vacuo
  2. filtrationthe residue was filtered over a short silica gel column (petroleum/acetone, 30:1)
  3. customAfter removal of the solvent in vacuo
  4. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-329465121cd744e299358f5deaf45108
Source dataset
uspto-grants-1996_09
Patent number
US05552550

Reaction notes

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