Selectfluor → (S)-ethyl 2-tert-butoxy-2-(6-chloro-4-fluoro-1-hydroxy-3-methylnaphthalen-2-yl)acetate

HRID 926147ノート

反応式

HRID 926147 の反応式
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:23])[CH:18]=2)[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)[F:26].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[C:20]([F:26])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:23])[CH:18]=2)[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:4])[CH3:3]

参加物

4

反応物 2

HCID 2724933SelectfluorHCID 89681780(S)-ethyl 2-tert-butoxy-2-(6-chloro-1-hydroxy-3-methylnaphthalen-2-yl)acetate

生成物 1

HCID 89681784(S)-ethyl 2-tert-butoxy-2-(6-chloro-4-fluoro-1-hydroxy-3-methylnaphthalen-2-yl)acetate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a solution of (S)-ethyl 2-tert-butoxy-2-(6-chloro-1-hydroxy-3-methylnaphthalen-2-yl)acetate (0.9705 g, 2.77 mmol) in anhydrous acetonitrile (20 mL) at 0° C. was added SelectFluor (1.078 g, 3.04 mmol) in one portion. The reaction mixture was stirred for 4 hours at 0° C., then 1 hour at room temperature. The reaction mixture was quenched with saturated Na2HPO4 solution and stirred for 20 minutes. The mixture was extracted with ethyl acetate (2×), dried (MgSO4), filtered, concentrated and stored overnight in a freezer. The residue was purified by flash column chromatography (silica gel, 0 to 15% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C19H21ClFO4: 367.8. Found: 366.9, 368.9.

後処理

  1. custom1 hour
  2. customat room temperature
  3. customThe reaction mixture was quenched with saturated Na2HPO4 solution
  4. stirringstirred for 20 minutes
  5. extractionThe mixture was extracted with ethyl acetate (2×)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. waitstored overnight in a freezer
  10. customThe residue was purified by flash column chromatography (silica gel, 0 to 15% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-b5a4f4c8128e47b2adc771c45f8973c5
出典データセット
uspto-grants-2016_03
特許番号
US09284323B2

反応ノート

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