Hydrochloric Acid → 1-(4-n-Propylphenyl)-2-trimethylsilylacetylene

HRID 493030

反応式

HRID 493030 の反応式
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)CC)C.Cl>[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 1363741-Bromo-4-propylbenzene

生成物 1

HCID 193534011-(4-n-Propylphenyl)-2-trimethylsilylacetylene収率 87.1%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒

実験手順

To 15.0 g (75.4 mmol) of 1-n-propyl-4-bromobenzene were added 8.8 g (89.8 mmol) of trimethylsilylacetylene and 100 ml of triethylamine (NEt3), and the reaction system was purged with argon. Next were added 81 mg (0.4 mmol) of copper (I) iodide (CuI), 324 mg (1.2 mmol) of triphenylphosphine, and 162 mg of dichlorobistriphenylphosphine palladium (II) [PdCl2(PPh3)2] to the reaction system, and the mixture was subjected to reaction for 24 hours with heating and refluxing. After completion of the reaction, the reaction mixture was poured into an iced water, and the resultant mixture was acidified by adding hydrochloric acid. After the resultant water-insoluble oil was extracted with hexane, the hexane phase was washed with water. By removing hexane from the hexane phase, 14.2 g (65.7 mmol) of 1-(4-n-propylphenyl)-2-trimethylsilylacetylene was obtained.

後処理

  1. customthe reaction system was purged with argon
  2. customthe mixture was subjected to reaction for 24 hours
  3. temperaturewith heating
  4. temperaturerefluxing
  5. customAfter completion of the reaction
  6. extractionAfter the resultant water-insoluble oil was extracted with hexane
  7. washthe hexane phase was washed with water
  8. customBy removing hexane from the hexane phase

出典と根拠

ORDレコード
ord-41c7fd2116914f8b8f5c9d25ee7d1452
出典データセット
uspto-grants-2009_05
特許番号
US07534547B2

関連ノート

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