Triisopropyl borate → HCID 18617068, compound

HRID 1263566Notes

Reaction equation

HRID 1263566 reaction equation
[CH2:1]([C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[O:6]C1CCCCO1)[CH:2]=[CH2:3].C([Li])(CC)C.C([O:25][B:26](OC(C)C)[O:27]C(C)C)(C)C>C1COCC1>[CH2:1]([C:4]1[C:5]([OH:6])=[C:13]([B:26]([OH:27])[OH:25])[CH:14]=[CH:15][CH:16]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 18617092HCID 18617092, compoundHCID 178418400CID 53628100

Product 1

HCID 18617068HCID 18617068, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-allylphenoxy)tetrahydropyran (3.5 g, 16.03 mmol) was dissolved in dry THF (120 ml) and the solution cooled to −78° C. sec-Butyl lithium (1.3M in hexanes, 14.7 ml, 19.11 mmol) was added dropwise with stirring over 10 minutes, the reaction was stirred at −78° C. for 2 hours. Triisopropoxy borane (6.7 ml, 28.77 mmol) was added and stirring continued for 4 hours at −78° C. The reaction was quenched with water, acidified to pH 1 with 2N hydrochloric acid and extracted with ether (2×200 ml). The combined extracts were dried with magnesium sulphate and concentrated under vacuum. The oily solid produced was triturated with cyclohexane and the solid filtered off to give the title compound (600 mg, 21%); MS 177 (M−H)−; HPLC retention time (system 1) 3.09 minutes.

Workup

  1. additionwas added dropwise
  2. stirringthe reaction was stirred at −78° C. for 2 hours
  3. stirringstirring
  4. waitcontinued for 4 hours at −78° C
  5. customThe reaction was quenched with water
  6. extractionextracted with ether (2×200 ml)
  7. dry with materialThe combined extracts were dried with magnesium sulphate
  8. concentrationconcentrated under vacuum
  9. customThe oily solid produced
  10. customwas triturated with cyclohexane
  11. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-02445d76abbf40218ab61b56c0619ee8
Source dataset
uspto-grants-2003_04
Patent number
US06541490B1

Reaction notes

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