Dimethylformamide → 3-[2-(4-{2-Methoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidin-3-ol

HRID 580959노트

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HRID 580959 반응식
Br[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]([O:6][CH2:7][CH2:8][O:9][CH3:10])=[C:4]([CH3:14])[CH:3]=1.[CH3:15][N:16]([CH3:19])[CH:17]=O>C(N(CC)CC)C.[OH-].[Na+].[Cu]I>[CH3:10][O:9][CH2:8][CH2:7][O:6][C:5]1[C:11]([CH3:13])=[CH:12][C:2]([C:3]#[C:4][C:5]2([OH:6])[CH:11]3[CH2:13][CH2:19][N:16]([CH2:17][CH2:12]3)[CH2:15]2)=[CH:3][C:4]=1[CH3:14]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 541527811-(4-Bromo-2,6-dimethylphenoxy)-2-methoxyethane

생성물 1

HCID 678504423-[2-(4-{2-Methoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidin-3-ol

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8471Triethylamine용매HCID 14798Sodium Hydroxide용매

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온도
65 °C

실험 절차

1-(4-bromo-2,6-dimethylphenoxy)-2-methoxyethane (704 mg) and copper (I) iodide (48 mg) in dimethylformamide (DMF) (5.5 ml) and triethylamine (2.7 ml) at ambient temperature and under an atmosphere of argon. The mixture was heated at 65° C. for 14 hours, cooled to ambient temperature, diluted with 2M aqueous sodium hydroxide (20 ml) and extracted with diethyl ether (5×100 ml). The ethereal extracts were combined, washed with water (100 ml) and saturated brine (100 ml), dried (K2CO3) and evaporated. The residue was crystallised from acetonitrile to give 3-[2-(4-{2-methoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidin-3-ol (130 mg) as a solid, m.p. 120° C.; microanaylsis, found: C, 72.4; H, 8.2; N, 4.1%; C2OH27NO3 requires: C, 72.9; H, 8.3; N, 4.2%; NMR([CD3)2SO): 1.3(1H,m), 1.57(1H,m), 1.9(3H,m), 2.21(6H,s), 2.65(4H,m), 2.8(1H,d), 3.02(1H,d), 3.31(3H,s), 3.61(2H,m), 3.87(2H,m), 5.5(1H,br) and 7.07(2H,s); m/z 330 (M+H).

후처리

  1. customat ambient temperature
  2. temperaturecooled to ambient temperature
  3. extractionextracted with diethyl ether (5×100 ml)
  4. washwashed with water (100 ml) and saturated brine (100 ml)
  5. dry with materialdried (K2CO3)
  6. customevaporated
  7. customThe residue was crystallised from acetonitrile

출처 및 근거

ORD 기록
ord-fbe52ca1885e4747bfdcb31e83805588
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919793

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