Ethylene Glycol → HCID 178517865, 화합물

HRID 215960노트

반응식

HRID 215960 반응식
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22](I)[CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)CCC.[Cu]I.O>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[C:24]([N:15]2[CH2:16][CH2:17][C:10]3([C:9](=[O:18])[N:8]([C@H:5]4[CH2:4][CH2:3][C@@H:2]([OH:1])[CH2:7][CH2:6]4)[CH2:12][CH2:11]3)[CH2:13][CH2:14]2)[CH:25]=1

참가 물질

8

반응물 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 178517868HCID 178517868, 화합물

생성물 1

HCID 178517865HCID 178517865, 화합물수율 70%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 2631-Butanol용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-(cis-4-hydroxycyclohexyl)-2,8-diazaspiro[4.5]decan-1-one (0.50 g, 2.0 mmol), 4-bromo-1-fluoro-2-iodobenzene (0.894 g, 2.97 mmol), copper(I) iodide (0.0586 g, 0.308 mmol), potassium phosphate (1.26 g, 0.596 mmol) and 1,2-ethanediol (0.23 mL, 4.1 mmol) in 1-butanol (2.5 mL) was heated at 100° C. overnight. The reaction mixture was treated with water, extracted with ether. The combined organic layers were washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure. The residue was purified on a silica gel column with ethyl acetate in hexane (gradient: 0 to 50%) to give the desired product (0.59 g, 70%). LCMS: (M+H)+=425.0/427.0.

후처리

  1. extractionextracted with ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified on a silica gel column with ethyl acetate in hexane (gradient: 0 to 50%)

출처 및 근거

ORD 기록
ord-d50c91e1934e43d382c73f612ede010c
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193207B2

반응 노트

불러오는 중…