HCID 67112061, compound → 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

HRID 2088920Notes

Reaction equation

HRID 2088920 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][C:7]([B:9]1[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]1)=[CH2:8])C=C>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.ClCCl>[O:4]1[CH2:1][CH:8]=[C:7]([B:9]2[O:10][C:11]([CH3:16])([CH3:17])[C:12]([CH3:14])([CH3:15])[O:13]2)[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 67112061HCID 67112061, compound

Product 1

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterYield 99%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Add Grubbs Catalyst, 2nd Generation (benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichloro(tricyclohexylphosphine)ruthenium, 2.58 g, 0.03 eq) to a solution of 2-(3-allyloxy-1-methylene-propyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (23.4 g, 98.26 mmol) in dichloromethane (280 mL) and stir for 16 hours. Concentrate in vacuo and add hexanes (120 mL) to the residue. Stir for one hour and filter. Concentrate the filtrate in vacuo to give 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a tan solid (20.4 g, 99%). 1H NMR (300 MHz, CDCl3) δ 6.50 (m, 1H), 4.17 (q, J=2.7 Hz, 2H), 3.73 (t, J=5.4 Hz, 2H), 2.20 (m, 2H), 1.24 (s, 12H).

Workup

  1. concentrationConcentrate in vacuo
  2. additionadd hexanes (120 mL) to the residue
  3. stirringStir for one hour
  4. filtrationfilter
  5. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-ac0580312bd24c83a6a123c285c746b4
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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