2-Bromoanisole → HCID 21187684, compound

HRID 1637076Notes

Reaction equation

HRID 1637076 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)[O:17][CH2:16]1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:21]1([OH:24])[CH2:22][CH2:23][C:18]2([O:25][CH2:15][CH2:16][O:17]2)[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 113582-BromoanisoleHCID 516892Sodium BicarbonateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 21187684HCID 21187684, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-Bromoanisole (1.87 g, 10.0 mmol) in 10 mL THF under Argon was added n-butyllithium (4.0 mL 2.5M in hexane, 10.0 mmol) cooled to -78° C. The solution was stirred 10 min. at -78° C., and a solution of 1,4-Cyclohexanedione mono-ethylene ketal (1.56 g, 10.0 mmol) in 10 mL THF was added slowly. The solution was warmed to r.t. and stirred for 60 min., then poured onto saturated sodium bicarbonate and extracted with ethylacetate. The combined organic layers were washed with saturated sodium chloride, dried with magnesium sulfate, and concentrated in vacuo. The crude solid was crystallized with hexane/diethylether 2:1 to give 8-(2-Methoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-8-ol as a white solid.

Workup

  1. temperatureThe solution was warmed to r.t.
  2. stirringstirred for 60 min.
  3. extractionextracted with ethylacetate
  4. washThe combined organic layers were washed with saturated sodium chloride
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude solid was crystallized with hexane/diethylether 2:1

Sources & evidence

ORD record
ord-cf48e51e396947a1a62fd0a0dda9931e
Source dataset
uspto-grants-2000_03
Patent number
US06037354

Reaction notes

Loading…