Triethylamine → 5-Phenoxy-1,2,3,4-tetrahydroquinoline

HRID 1172998

반응식

HRID 1172998 반응식
[NH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[CH2:4][CH2:3][CH2:2]1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][CH2:2][NH:1]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 30460361,2,3,4-Tetrahydroquinolin-5-ol

생성물 1

HCID 4875475-Phenoxy-1,2,3,4-tetrahydroquinoline수율 17%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 0.15 g (1.01 mmol) 1,2,3,4-tetrahydro-quinolin-5-ol in 10 ml dichloromethane were added 0.17 g (1.40 mmol) phenylboronic acid, 0.25 g (1.36 mmol) copper(II) acetate, a spatula end of 4 Å molecular sieves and 0.57 ml (4.52 mmol) triethylamine. The reaction mixture was stirred at room temperature for 72 h and then filtered through celite, washing with dichloromethane. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient) to afford 34 mg (17%) of the title compound as a pink oil. MS (ISP): 226.3 ([M+H]+).

후처리

  1. filtrationfiltered through celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

출처 및 근거

ORD 기록
ord-644eeb8470344990ba30236f052007a5
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834044B2

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