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Triethylamine → 4,4,7-Trimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester

HRID 1765897
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HRID 1765897 반응식
[CH2:1]([O:3][C:4]([CH:6]1[C:15]2[C:10](=[CH:11][C:12](OS(C(F)(F)F)(=O)=O)=[C:13]([CH3:16])[CH:14]=2)[C:9]([CH3:26])([CH3:25])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:34][Si:35]([C:38]#[CH:39])([CH3:37])[CH3:36].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>[CH2:1]([O:3][C:4]([CH:6]1[C:15]2[C:10](=[CH:11][C:12]([C:39]#[C:38][Si:35]([CH3:37])([CH3:36])[CH3:34])=[C:13]([CH3:16])[CH:14]=2)[C:9]([CH3:26])([CH3:25])[CH2:8][CH2:7]1)=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl Acetate2회HCID 66111TrimethylsilylacetyleneHCID 588834474,4,7-Trimethyl-6-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester2회

생성물 1

HCID 690745094,4,7-Trimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester수율 34.5%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8058Hexane용매2회

실험 절차

Following General Procedure D in a sealed tube and using 4,4,7-trimethyl-6-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester (Intermediate 192, 0.86 g, 2.2 mmol), triethyl amine (2 mL), copper(I)iodide (0.083 g, 0.44 mmol), trimethylsilyl acetylene (2 mL, 14 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.306 g, 0.44 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 5% ethyl acetate in hexane as the eluent, and preaprative normal phase HPLC using 5% ethyl acetate in hexane as the mobile phase in order to separate recovered starting material from the product, the title compound (0.26 g) was obtained.

후처리

  1. customto separate
  2. customrecovered

출처 및 근거

ORD 기록
ord-7a455cee58184d9ab8edd9a87a9db979
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07226951B2

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