3-Butyn-1-OL → HCID 67402660、化合物

HRID 906108ノート

反応式

HRID 906108 の反応式
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]

参加物

6

反応物 2

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

生成物 1

HCID 67402660HCID 67402660、化合物収率 15%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-e10546838e9f4573a9e9891932eb9656
出典データセット
uspto-grants-2011_09
特許番号
US08012956B2

反応ノート

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