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

HRID 2377333노트

반응식

HRID 2377333 반응식
[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]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 574242146-Bromo-8-hydroxy-2,2,4,4-tetramethyl chroman2회

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8058Hexane용매

실험 절차

Following General Procedure D and using 6-bromo-8-hydroxy-2,2,4,4-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.

출처 및 근거

ORD 기록
ord-a721d3d2852b4ac4bc88c2b375997799
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468391B2

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