3-Butyn-1-OL → HCID 67402660, 화합물

HRID 906108노트

반응식

HRID 906108 반응식
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:14]([OH:18])[CH2:15][C:16]#[CH:17]>C(N(CC)CC)C.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.[Cu]I>[OH:18][CH2:14][CH2:15][C:16]#[C:17][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

6

반응물 2

HCID 135663-Butyn-1-OLHCID 10922803methyl 2-bromo-3-methoxybenzoate

생성물 1

HCID 67402660HCID 67402660, 화합물수율 15%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

A mixture of methyl 2-bromo-3-methoxybenzoate (0.4 g, 1.63 mmol), Pd(PPh3)2Cl2 (0.057 g, 0.082 mmol), copper (I) iodide (0.031 g, 0.16 mmol) and 3-butyn-1-ol (0.173 ml, 2.28 mmol) were stirred in trietylamine (5 ml) at 80° C. for 20 h. The solvent was concentrated under vacuum, and the residue was partitioned between ethyl acetate (15 ml) and water (5 ml). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using hexanes:ethyl acetate 2:1 as eluent to afford methyl 2-(4-hydroxybut-1-yn-1-yl)-3-(methyloxy)benzoate (0.056 g; 15% yield). MS (EI) for C13H14O4: 235 (MH+).

후처리

  1. concentrationThe solvent was concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate (15 ml) and water (5 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e10546838e9f4573a9e9891932eb9656
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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