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Dichloromethane → Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(3,3-dimethylbutyl)amino]-2-fluorobenzoate

HRID 551953
ノート
印刷プレビュー

反応式

HRID 551953 の反応式
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:31]=[CH:30][C:16]([CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([O:26][CH3:27])=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:32][C:33]([CH3:38])([CH3:37])[CH2:34][CH:35]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClCCl>ClCCCl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][N:18]([CH2:35][CH2:34][C:33]([CH3:38])([CH3:37])[CH3:32])[C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([O:26][CH3:27])=[O:25])=[CH:30][CH:31]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 763353,3-DimethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 11452740Methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate

生成物 1

HCID 67170689Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(3,3-dimethylbutyl)amino]-2-fluorobenzoate収率 56.1%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
70 °C

実験手順

Methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate (800 mg, 1.93 mmol) was dissolved in DCE (15 mL), then 3,3-dimethyl-butyraldehyde (289 mg, 2.89 mmol) was added followed by sodium triacetoxyborohydride (Aldrich, 1224 mg, 5.78 mmol) and the resulting mixture stirred at 70° C. for 2 h. Reaction was allowed to cool down, dichloromethane (40 mL) was added and the organic layer was washed twice with H2O and once with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification on silicagel afforded 541 mg (56%) of the title compound as a colorless oil. HPLC, Rt: 6.42 min, purity: 98.3%); LC/MS, M+(ESI): 500.4; 1H NMR (CDCl3) δ: 7.44 (m, 4H), 7.17 (m, 5H), 6.93 (t, J=9.6 Hz, 1H), 6.73 (m, 1H), 4.46 (s, 2H), 3.88 (s, 3H), 3.40 (m, 2H), 2.60 (t, J=7.7 Hz, 2H), 1.70-1.46 (m, 4H), 1.34 (m, 2H), 0.99-0.87 (m, 12H).

後処理

  1. customReaction
  2. temperatureto cool down
  3. washthe organic layer was washed twice with H2O and once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification on silicagel

出典と根拠

ORDレコード
ord-7c11ced0411546f9bd321a8ed8a98987
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07947851B2

反応ノート

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