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

HRID 580959ノート

反応式

HRID 580959 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8471Triethylamine溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fbe52ca1885e4747bfdcb31e83805588
出典データセット
uspto-grants-1999_07
特許番号
US05919793

反応ノート

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