Dimethyl (2-propynyloxy)(1,1,2-trimethylpropyl)-silane → (4-Bromo-2-{3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-prop-1-ynyl}-5-methyl-phenyl)-carbamic acid methyl ester

HRID 1760584ノート

反応式

HRID 1760584 の反応式
[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1I.[CH3:15][Si:16]([CH3:27])([O:23][CH2:24][C:25]#[CH:26])[C:17]([CH3:22])([CH3:21])[CH:18]([CH3:20])[CH3:19]>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1[C:26]#[C:25][CH2:24][O:23][Si:16]([CH3:27])([CH3:15])[C:17]([CH3:22])([CH3:21])[CH:18]([CH3:20])[CH3:19]

参加物

4

反応物 2

HCID 18455989Dimethyl (2-propynyloxy)(1,1,2-trimethylpropyl)-silaneHCID 57543475Methyl (4-Bromo-2-iodo-5-methylphenyl)carbamate

生成物 1

HCID 68890098(4-Bromo-2-{3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-prop-1-ynyl}-5-methyl-phenyl)-carbamic acid methyl ester

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

To a solution of 3.70 g (4-bromo-2-iodo-5-methyl-phenyl)-carbamic acid methyl ester and 0.070 g bis-triphenylphosphine palladium dichloride and 0.038 g cuprous iodide in 25 mL triethylamine was added 2.38 g dimethyl (2-propynyloxy)(1,1,2-trimethylpropyl)-silane and the mixture was heated 2 h at reflux. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was washed with 1N hydrochloric acid, sodium bicarbonate and brine, dried with magnesium sulfate and purified by chromatography on silica gel with 4:1 hexane:ethyl acetateto yield 1.92 g of the title compound as a light brown oil. MS: M+NH4+=457.0 M+Na+=462.2.

後処理

  1. temperaturethe mixture was heated 2 h
  2. temperatureat reflux
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customThe phases were separated
  5. washthe organic phase was washed with 1N hydrochloric acid, sodium bicarbonate and brine
  6. dry with materialdried with magnesium sulfate
  7. custompurified by chromatography on silica gel with 4:1 hexane

出典と根拠

ORDレコード
ord-f8ab1de3937a4bbf88b38e5b6cbc4a05
出典データセット
uspto-grants-2005_01
特許番号
US06844345B2

反応ノート

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