Sodium borohydride → 5,5-Dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol

HRID 1523417ノート

反応式

HRID 1523417 の反応式
[CH3:1][C:2]1([CH3:18])[CH2:7][C:6](=[O:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([OH:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 592264755,5-Dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone

生成物 1

HCID 592264895,5-Dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol収率 74%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone (1.0 eq), and CeCl3-7H2O (1.2 eq) in MeOH (0.2 M) was added NaBH4 (1.0 eq) at 0° C. The solution was stirred for 1 hour, and then quenched by the addition of 5 mL of water. The volatiles were removed in vacuum and the residue was partitioned between EtOAc and H2O. The organic layer was separated and washed with brine. The combined aqueous was back extracted with EtOAc and the organic was washed with brine. The combined organics were dried over MgSO4, filtered and concentrated. The residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes) to give 5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (74%). LC/MS (m/z): MH+=249.2, Rt=0.76.

後処理

  1. customquenched by the addition of 5 mL of water
  2. customThe volatiles were removed in vacuum
  3. customthe residue was partitioned between EtOAc and H2O
  4. customThe organic layer was separated
  5. washwashed with brine
  6. extractionThe combined aqueous was back extracted with EtOAc
  7. washthe organic was washed with brine
  8. dry with materialThe combined organics were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes)

出典と根拠

ORDレコード
ord-0f58b22a14214570a171fba4e3228c79
出典データセット
uspto-grants-2015_07
特許番号
US09079889B2

反応ノート

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