Isobutylene → 7-Tert-butoxy-1-nitronaphthalene

HRID 2306234Notes

Reaction equation

HRID 2306234 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[N+:5]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[CH:16]=[C:15]([OH:18])[CH:14]=[CH:13]2)([O-:7])=[O:6].FC(F)(F)S(O)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[C:2]([O:18][C:15]1[CH:16]=[C:17]2[C:12]([CH:11]=[CH:10][CH:9]=[C:8]2[N+:5]([O-:7])=[O:6])=[CH:13][CH:14]=1)([CH3:3])([CH3:1])[CH3:4]

Participants

6

Reactant 4

HCID 8255IsobutyleneHCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 158773508-Nitro-2-naphthol

Product 1

HCID 184336007-Tert-butoxy-1-nitronaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

Isobutylene (150 mL) was condensed into a stirred mixture of 8-nitro-2-naphthol, as described above in Step C, (4.35 g, 23.0 mmol) in CH2Cl2 (200 mL) at −78° C. Trifluoromethanesulfonic acid (0.203 mL, 2.30 mmol) was added and the mixture was allowed to slowly warm to −20° C. over about 4 hours. Triethylamine (2.56 mL, 18.4 mmol) was added and the mixture was allowed to warm to ambient temperature, then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica, eluting with hexane—5% EtOAc to yield the titled product.

Workup

  1. customcondensed
  2. temperatureto warm to ambient temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash column chromatography on silica
  5. washeluting with hexane—5% EtOAc

Sources & evidence

ORD record
ord-b8447f05f73942669ca8524e16ba33c6
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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