Water → Methyl 4-(3-hydroxyprop-1-ynyl)benzoate

HRID 352605

반응식

HRID 352605 반응식
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([OH:15])[C:13]#[CH:14].C(N(CC)CC)C.O>C(#N)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>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([C:14]#[C:13][CH2:12][OH:15])=[CH:3][CH:4]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 69273Methyl 4-iodobenzoate

생성물 1

HCID 4448596Methyl 4-(3-hydroxyprop-1-ynyl)benzoate수율 87.5%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

To a solution of methyl 4-iodobenzoate (20 g, 76 mmol), propargyl alcohol (5.55 g, 99.0 mmol) and triethylamine (20 mL) in acetonitrile (200 mL) was added dichlorobis(triphenylphosphine)palladium(II) (1.55 g, 2.21 mmol), followed by Cul (454 mg, 2.38 mmol). The reaction mixture was stirred at room temperature for 24 h. Water was added and the aqueous solution was washed with EtOAc (3×). The organic solutions were combined, dried (MgSO4), filtered and concentrated. Purification by medium pressure chromatography (9:1 hexanes:EtOAc to 4:1 hexanes:EtOAc) provided 4-(3-hydroxy-prop-1-ynyl)-benzoic acid methyl ester (12.65 g).

후처리

  1. washthe aqueous solution was washed with EtOAc (3×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by medium pressure chromatography (9:1 hexanes:EtOAc to 4:1 hexanes:EtOAc)

출처 및 근거

ORD 기록
ord-e61a163fbe4346efb57e0fd0ad0b776b
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747054B2

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