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

HRID 1765870노트

반응식

HRID 1765870 반응식
[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

참가 물질

9

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86600196Trifluoro-methanesulfonic acid 4-cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester2회

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

출처 및 근거

ORD 기록
ord-61c67f29b073410798af5de2557a6185
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226951B2

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