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

HRID 449129

반응식

HRID 449129 반응식
[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

참가 물질

7

반응물 4

HCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 742994-Chlorophenylboronic acidHCID 218772022-Aminocyclohexanol hydrochlorideHCID 45051731Sodium hexamethyidisilazane

생성물 1

HCID 116440892-(4-Chloro-benzyl)-tetrahydrofuran

시약·촉매·용매 2

HCID 26038Nickel(II) iodide촉매HCID 3776Isopropanol용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8671103c7cc1408b9ba4f571600f3510
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481733B2

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