2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (E)-2,2-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pent-4-en-1-ol

HRID 889263Notes

Reaction equation

HRID 889263 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:5][CH:6]=[CH2:7])[CH2:3][OH:4].[CH3:9][C:10]1([CH3:19])[C:14]([CH3:16])([CH3:15])[O:13][B:12](C=C)[O:11]1>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:1][C:2]([CH3:8])([CH2:5]/[CH:6]=[CH:7]/[B:12]1[O:13][C:14]([CH3:16])([CH3:15])[C:10]([CH3:19])([CH3:9])[O:11]1)[CH2:3][OH:4]

Participants

5

Reactant 2

HCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 107491582,2-Dimethylpent-4-en-1-ol

Product 1

HCID 68431549(E)-2,2-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pent-4-en-1-ol

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2,2-dimethylpent-4-en-1-ol (4.9 g, 42.9 mmol) in DCM (500 mL) is added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (22 mL, 128 mmol) and Grubbs catalyst (3.53 g, 4.29 mmol), and the mixture is heated at 40° C. for 18 h. The mixture is concentrated and washed with sat. NaHCO3 and purified to give the title compound as a greenish crystalline.

Workup

  1. concentrationThe mixture is concentrated
  2. washwashed with sat. NaHCO3
  3. custompurified

Sources & evidence

ORD record
ord-0024ec0f369d44e994f9639049b22e01
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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