Tetrahydrofuran → 8-Cyclopropyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-1-tetralone

HRID 2377485ノート

反応式

HRID 2377485 の反応式
[CH:1]1([C:4]2[C:13]3[C:12](=[O:14])[CH2:11][CH2:10][C:9]([CH3:16])([CH3:15])[C:8]=3[CH:7]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.O1CCCC1.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>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.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])[CH:7]=[C:8]3[C:13]=2[C:12](=[O:14])[CH2:11][CH2:10][C:9]3([CH3:16])[CH3:15])[CH2:3][CH2:2]1

参加物

9

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86600196Trifluoro-methanesulfonic acid 4-cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester2 回

生成物 1

HCID 211072428-Cyclopropyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-1-tetralone

試薬・触媒・溶媒 4

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HCID 8857Ethyl Acetate溶媒

実験手順

Following General Procedure B and using trifluoro-methanesulfonic acid 4-cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl ester (Intermediate 158, 1.09 g, 3 mmol), triethyl amine (5 mL), tetrahydrofuran (5 mL), copper(I)iodide (0.12 g, 0.6 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.42 g, 0.6 mmol) and (trimethylsilyl)acetylene (2.2 mL, 15 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 7% ethyl acetate in hexane as the eluent, the title compound was obtained as an orange oil (1.05 g, quantitative).

出典と根拠

ORDレコード
ord-8a896c822b264e2191769c208ae263b0
出典データセット
uspto-grants-2008_12
特許番号
US07468391B2

反応ノート

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