2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(3,4-Dimethoxy-2-methoxymethoxyphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

HRID 895398Notes

Reaction equation

HRID 895398 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][O:11][CH3:12])[C:4]=1[O:13][CH3:14].C([Li])CCC.C(O[B:24]1[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]1)(C)C>C(OCC)C>[CH3:14][O:13][C:4]1[C:5]([O:9][CH2:10][O:11][CH3:12])=[C:6]([B:24]2[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 109979631,2-Dimethoxy-3-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 223807722-(3,4-Dimethoxy-2-methoxymethoxyphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

The MOM-protected phenol 1a (10 g; 0.0505 mol) was dissolved in 1000 ml of dry diethyl ether and cooled to −78° C. A solution of n-butyl lithium (22.2 ml of 2.5 M) was then added via syringe. The cooling bath was removed and the solution was allowed to warm to room temperature. After stirring the solution at room temperature for two hours, a yellow precipitate was observed. The mixture was cooled to −78° C., and 15 ml of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.080 mol) was added via syringe. The cooling bath was removed after two hours. Stirring was continued for four hours at room temperature. The mixture was then poured into 300 ml of water and extracted several times with diethyl ether (3×300 ml), dried (Na2SO4), and concentrated to a yellow oil (12.37 g, 76%) that was used without further purification: 1H NMR: (300 MHz, CDCl3): 7.46 (d, 1H, J=8.4 Hz); 6.69 (d, 1H, J=8.4 Hz); 5.15 (s, 2H); 3.87 (s, 3H); 3.83 (s, 3H); 1.327 (s, 12H).

Workup

  1. customThe cooling bath was removed
  2. temperatureto warm to room temperature
  3. temperatureThe mixture was cooled to −78° C.
  4. customThe cooling bath was removed after two hours
  5. stirringStirring
  6. waitwas continued for four hours at room temperature
  7. additionThe mixture was then poured into 300 ml of water
  8. extractionextracted several times with diethyl ether (3×300 ml)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated to a yellow oil (12.37 g, 76%) that
  11. customwas used without further purification

Sources & evidence

ORD record
ord-260ea723dd1a4360846263d806980cf9
Source dataset
uspto-grants-2005_07
Patent number
US06916823B2

Reaction notes

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