Furan, 2-(bromomethyl)tetrahydro- → 2-(4-Chloro-benzyl)-tetrahydrofuran

HRID 449129

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Cl.N[CH:13]1[CH2:18][CH2:17][CH2:16]C[CH:14]1[OH:19].C[Si](C)(C)N[Si](C)(C)C.[Na].BrCC1CCCO1>CC(O)C.[Ni](I)I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:16][CH:17]2[CH2:18][CH2:13][CH2:14][O:19]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred mixture of (4-chlorophenyl)dihydroxyborane (524.0 mg, 3.351 mmol), 2-aminocyclohexanol hydrochloride (42 mg, 0.28 mmol) and nickel iodide (87.3 mg, 0.279 mmol) in i-PrOH (10.00 mL) was added sodium hexamethyldisilazane (1.075 g, 5.864 mmol) at 0° C. Then the mixture was stirred at rt for 5 min before 2-bromomethyl-tetrahydro-furan (460.00 mg, 2.80 mmol) was added by syringe. The resulting mixture was then stirred at 60° C. for 5 h. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography(5% AcOEt in hexane).

Workup

additionwas added by syringe
customThe solvent was then removed under reduced pressure
customthe resulting residue was purified by a flash chromatography(5% AcOEt in hexane)

Sources & evidence

ORD record: ord-8671103c7cc1408b9ba4f571600f3510
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481733B2

Linked notes

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