Propargyl alcohol → Methyl 4-(3-hydroxyprop-1-ynyl)benzoate

HRID 430530

反応式

HRID 430530 の反応式
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(NCC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:15][CH2:12][C:13]#[C:14][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 7859Propargyl alcoholHCID 69273Methyl 4-iodobenzoate

生成物 1

HCID 4448596Methyl 4-(3-hydroxyprop-1-ynyl)benzoate収率 83.1%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8021Diethylamine溶媒

実験手順

Methyl 4-iodobenzoate (9.0 g, 34.4 mmol) was dissolved in 90 ml of diethylamine. The solution was stirred vigorously and, sequentially, 121 milligrams of bis(triphenylphosphine) palladium chloride and 65 milligrams of cuprous iodide were added, each in a single portion, followed by 1.93 grams of propargyl alcohol. The resultant mixture was stirred for about 20 hours at room temperature in an argon atmosphere. At the end of this period, diethylamine Was removed by concentration in vacuo. The residue was diluted with 200 ml of water and extracted three times with 100 ml of benzene and 75 ml of ethyl acetate. The organic extracts were combined, dried over Na2SO4, and concentrated in vacuo, yielding a brown solid. This crude residue was purified by flash chromatography. Elution with a 2 to 1 (V:V) mixture of hexane and ethyl acetate yielded 5.44 grams (83% yield) of a pale yellow solid melting at 81 to 82° C.

後処理

  1. customAt the end of this period, diethylamine Was removed by concentration in vacuo
  2. additionThe residue was diluted with 200 ml of water
  3. extractionextracted three times with 100 ml of benzene and 75 ml of ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customyielding a brown solid
  7. customThis crude residue was purified by flash chromatography
  8. washElution with a 2
  9. additionto 1 (V:V) mixture of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-a03ea6fc0e5e4faa9636c7211f3aca32
出典データセット
uspto-grants-2001_11
特許番号
US06323210B2

関連ノート

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