1,2-Ethanedithiol → 2-Chloro-4-(hydroxymethyl)-3-methylbenzonitrile
Reaction equation
[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]Participants
5
Conditions
- Temperature
- 70 °C
Procedure
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]+.
Workup
- customTo a pressure reaction flask
- customIt was sealed
- temperaturecooled to RT
- concentrationThe reaction mixture was concentrated
- dissolutiondissolved in EtOAc
- washwashed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customRecrystallization in EtOAc/hexanes
Sources & evidence
- ORD record
- ord-6f973348b7b245bc91aa790a6ac3c759
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696241B2
Reaction notes
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