2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 5-(Cyclopropylmethoxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzodioxole

HRID 1423407Notes

Reaction equation

HRID 1423407 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]3[O:10][CH2:11][O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.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>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]3[O:10][CH2:11][O:12][C:8]=3[C:7]=2[B:24]2[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66866695HCID 66866695, compoundHCID 178418339Butyllithium

Product 1

HCID 668666985-(Cyclopropylmethoxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction is performed in flame-dried glassware under an atmosphere of argon. A stirred solution of 5-cyclopropylmethoxy-benzo[1,3]dioxole from example B.b1 (38.44 g; 200.0 mmol) in dry THF (500 mL) is cooled to −40° C. before n-butyl lithium (138.0 mL; 1.6 M solution in hexane; 220 mmol) is slowly added via syringe. After complete addition, stirring is continued at −40° C. for two hours. At −78° C. neat 2-iso-propoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (40.95 g; 220.0 mmol) is added via syringe and stirring is continued at −78° C. for two hours.

Workup

  1. additionis slowly added via syringe
  2. additionAfter complete addition
  3. stirringstirring
  4. waitis continued at −78° C. for two hours

Sources & evidence

ORD record
ord-128431841cb847c99c300280ba859e38
Source dataset
uspto-grants-2015_01
Patent number
US08927557B2

Reaction notes

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