Triisopropyl borate → HCID 59816160, compound

HRID 1176816Notes

Reaction equation

HRID 1176816 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][CH3:14])=[CH:7][CH:6]=1.[Li]C(CC)C.[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C>C1COCC1>[CH3:14][O:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][C:7]=1[B:20]([OH:25])[OH:21]

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 5426431,4-Bis-methoxymethoxy-benzeneHCID 178418400CID 53628100

Product 1

HCID 59816160HCID 59816160, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of 1,4-bis-methoxymethoxy-benzene 5 (12.0 g, 60.6 mmol) in dry THF (250 mL) to −78° C. Add s-BuLi (1.3 M in hexane, 51 mL, 66.6 mmol) dropwise. Stir the reaction for 15 minutes and then add triisopropyl borate (14.2 mL, 60.6 mmol) slowly. Stir the reaction at −78° C. for 1 hour and warm to room temperature. Quench the reaction with 10% HCl and stir for 10 minutes. Extract with EtOAc (2×). Dry combined organic extracts (Na2SO4), filter, and concentrate in vacuo. Purify by flash chromatography (250 g SiO2, 20-50% EtOAc/hexanes and then 50% EtOAc/hexanes) to give 2,5-Bis-methoxymethoxy phenylboronic acid 7 (9.73 g, 40.2 mmol, 66%) as a yellow solid. 1H NMR (δ, 400 MHz, CDCl3): 7.50 (d, J=2.0 Hz, 1H), 7.09-7.07 (m, 2H), 5.93 (s, 2H), 5.24 (s, 2H), 5.14 (s, 2H), 3.49 (s, 3H), 3.48 (s, 3H). LRMS calcd, for C10H14 BO6: 241.0; found (electrospray, M−1) 241.0.

Workup

  1. customthe reaction for 15 minutes
  2. stirringStir
  3. customthe reaction at −78° C. for 1 hour
  4. customQuench
  5. customthe reaction with 10% HCl
  6. stirringstir for 10 minutes
  7. extractionExtract with EtOAc (2×)
  8. customDry
  9. filtrationfilter
  10. concentrationconcentrate in vacuo
  11. customPurify by flash chromatography (250 g SiO2, 20-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-8d3bca15507c4b48817863c7468f6626
Source dataset
uspto-grants-2010_11
Patent number
US07842822B2

Reaction notes

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