Tetrahydrofuran → 8-Ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman

HRID 51689노트

반응식

HRID 51689 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:12][CH3:13])[CH:11]=1)[O:8][C:7]([CH3:15])([CH3:14])[CH2:6][C:5]2([CH3:17])[CH3:16].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20].C(N(CC)CC)C.O1CCCC1>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>[CH2:12]([C:10]1[CH:11]=[C:2]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])[CH:3]=[C:4]2[C:9]=1[O:8][C:7]([CH3:15])([CH3:14])[CH2:6][C:5]2([CH3:17])[CH3:16])[CH3:13]

참가 물질

9

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 695485316-Bromo-8-ethyl-2,2,4,4-tetramethyl chroman2회

생성물 1

HCID 695486138-Ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman

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 D and using 6-bromo-8-ethyl-2,2,4,4-tetramethyl chroman (Intermediate 46, 0.5 g, 1.61 mmol), (trimethylsilyl)acetylene (1.57 g, 16.1 mmol), triethyl amine (8 mL), anhydrous tetrahydrofuran (10 mL), copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.075 g, 0.11 mmol), followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.137 g, 27%).

출처 및 근거

ORD 기록
ord-21c959cdebb142968edc971312669324
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713647B2

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