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

HRID 642748

반응식

HRID 642748 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 685775712-Chloro-4-(hydroxymethyl)-3-methylbenzonitrile수율 66.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-6f973348b7b245bc91aa790a6ac3c759
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696241B2

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