Triethylamine → [4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-carbamic acid tert-butyl ester

HRID 1069184ノート

反応式

HRID 1069184 の反応式
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:23][C:24]([CH3:28])([CH3:27])[C:25]#[CH:26]>C1COCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:26]#[C:25][C:24]([CH3:28])([CH3:27])[CH3:23])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 2773612tert-butyl N-(4-iodophenyl)carbamate

生成物 1

HCID 54041145[4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

(4-Iodo-phenyl)-carbamic acid tert-butyl ester (37a, 1.0 g, 3.13 g) was dissolved in THF (30 mL) and treated with Et3N (2.2 mL, 15.7 mmol), 3,3-dimethyl- 1-butyne (0.58 mL, 4.70 mmol), bis(triphenylphosphine) palladium (II) chloride (0.218 g, 0.31 mmol), and copper (I) iodide (0.03 g, 0.16 mmol). The reaction was stirred overnight at room temperature, then filtered and concentrated. The residue was chromatographed on silica gel eluting with 8:1 hexanes/EtOAc to give 0.7 g (82%) of the mostly clean desired product which was carried on without further purification.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was chromatographed on silica gel eluting with 8:1 hexanes/EtOAc

出典と根拠

ORDレコード
ord-b7f7edb3e6ca4fadb3e54c6928262d62
出典データセット
uspto-grants-2001_06
特許番号
US06251919B1

反応ノート

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