Triethylamine → 6-Bromo-8-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman

HRID 1765723ノート

反応式

HRID 1765723 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](O)[CH:11]=1)[O:8][C:7]([CH3:14])([CH3:13])[CH2:6][C:5]2([CH3:16])[CH3:15].C(N(CC)CC)C.[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26].C(OCC)(=O)C>CCCCCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])[CH:11]=1)[O:8][C:7]([CH3:14])([CH3:13])[CH2:6][C:5]2([CH3:16])[CH3:15]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 574242146-Bromo-8-hydroxy-2,2,4,4-tetramethyl chroman

生成物 1

HCID 574242166-Bromo-8-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman収率 100%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8058Hexane溶媒

実験手順

Following General Procedure D and using 6-bromo-8-hydroxy-2,2,24,4-tetramethyl chroman (Intermediate 17, 1.0 g, 3.51 mmol), triethyl amine (5 mL), copper(I)iodide (0.066 g, 0.351 mmol), trimethylsilyl acetylene (2.5 mL, 17.6 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.246 g, 0.351 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 0.5% ethyl acetate in hexane as the eluent, the title compound (1.08 g,˜100%) was obtained as a brown oil.

出典と根拠

ORDレコード
ord-528353526096429789c8c06969c23368
出典データセット
uspto-grants-2007_06
特許番号
US07226951B2

反応ノート

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