1,2-Ethanedithiol → 2-Chloro-4-(hydroxymethyl)-3-methylbenzonitrile

HRID 642748

反応式

HRID 642748 の反応式
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[N:13])[C:5](OC)=[O:6].C(S)CS.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH2:5][OH:6])[CH:9]=[CH:10][C:11]=1[C:12]#[N:13]

参加物

5

反応物 3

HCID 109021,2-EthanedithiolHCID 4311764Sodium borohydrideHCID 68579417Methyl 3-chloro-4-cyano-2-methylbenzoate

生成物 1

HCID 685775712-Chloro-4-(hydroxymethyl)-3-methylbenzonitrile収率 66.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a pressure reaction flask containing compound 7A (1.5 g, 7.2 mmol) in THF (30 mL) were added 1,2-ethanedithiol (2.4 g, 28.6 mmol) and NaBH4 (812 mg, 21.5 mmol). It was sealed, and heated at 70° C. for 2 hr, and cooled to RT. The reaction mixture was concentrated, dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. Recrystallization in EtOAc/hexanes give the title compound (870 mg). (ES) m/z 182 [M+H]+; 204 [M+Na]+.

後処理

  1. customTo a pressure reaction flask
  2. customIt was sealed
  3. temperaturecooled to RT
  4. concentrationThe reaction mixture was concentrated
  5. dissolutiondissolved in EtOAc
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customRecrystallization in EtOAc/hexanes

出典と根拠

ORDレコード
ord-6f973348b7b245bc91aa790a6ac3c759
出典データセット
uspto-grants-2010_04
特許番号
US07696241B2

関連ノート

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