Boron trifluoride etherate → HCID 86690107, compound

HRID 520398Notes

Reaction equation

HRID 520398 reaction equation
C(O[CH:5]1[CH2:10][CH2:9][CH:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][O:6]1)(=O)C.[CH3:19][O:20][C:21]([O:25][Si](C)(C)C)=[C:22]([CH3:24])[CH3:23].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:12]([O:11][CH:8]1[CH2:7][O:6][CH:5]([C:22]([CH3:24])([CH3:23])[C:21]([O:20][CH3:19])=[O:25])[CH2:10][CH2:9]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 15507553HCID 15507553, compound

Product 1

HCID 86690107HCID 86690107, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(benzyloxy)tetrahydro-2H-pyran-2-yl acetate (281 mg, 1.123 mmol) and ((1-methoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane (783 mg, 4.49 mmol) in DCM (5 mL) at −78° C. was added BF3.OEt2 (0.228 mL, 1.796 mmol). The reaction mixture was gradually allowed to warm to rt and stirred at rt for 18 h. The reaction mixture was quenched with sat. NaHCO3 (5 mL) and diluted with DCM (20 mL). The organic layer was separated, washed with water, brine, dried (MgSO4) and concentrated. The crude product was purified by silica gel FCC (10-20% EtOAc in hexanes) to afford methyl 2-(5-(benzyloxy)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate as a colorless oil (253 mg). To a solution of methyl 2-(5-(benzyloxy)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate (250 mg) in MeOH (20 mL) was added 10% Pd—C (59.7 mg) and the reaction mixture was hydrogenated at 40 psi overnight. The suspension was filtered and the filtrate was evaporated to dryness to afford methyl 2-(5-hydroxytetrahydro-2H-pyran-2-yl)-2-methylpropanoate as a clear oil (188 mg).

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3 (5 mL)
  2. additiondiluted with DCM (20 mL)
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel FCC (10-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b4ff093d1e8f4e2886ce80f7767335c1
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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