Water → 2-(2-Bromo-5-fluoro-pyridin-4-yl)-propane-1,2-diol

HRID 474079ノート

反応式

HRID 474079 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[C:5]([F:11])=[CH:4][N:3]=1.C[N+]1([O-])CC[O:16]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH2:28]>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([OH:16])([CH3:10])[CH2:9][OH:28])[C:5]([F:11])=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 866680492-Bromo-5-fluoro-4-isopropenyl-pyridine

生成物 1

HCID 866680502-(2-Bromo-5-fluoro-pyridin-4-yl)-propane-1,2-diol

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 2-bromo-5-fluoro-4-isopropenyl-pyridine (17.1 g, 79 mmol) in acetone (50 mL) and H2O (100 mL) was added N-methylmorpholine oxide (10.51 g, 87 mmol) and OSO4 (4.97 mL, 4.02 g, 0.396 mmol). The biphasic mixture was stirred at rt for 17 h. The reaction mixture was quenched with sodium hydrosulfite (1.516 g, 8.71 mmol) in H2O (50 ml) and stirred at rt for 20 min. The reaction mixture was filtered through celite and the celite pad was washed three times with acetone. The combined filtrates were evaporated and the residue was taken up with EtOAc and 1N aq. NaOH soln. The phases were separated and the aq. phase was reextracted with EtOAc. The combined org. phases were dried over Na2SO4, filtered and concentrated to yield the title compound as a light purple solid. HPLC RtH4=0.60 min; ESIMS: 250, 252 [(M+H)+]; 1H NMR (400 MHz, DMSO-d6): δ 8.32 (d, 1H), 7.71 (d, 1H), 5.57 (s, 1H), 4.89 (t, 1H), 3.65-3.57 (m, 1H), 3.53-3.45 (m, 1H), 1.39 (s, 3H).

後処理

  1. stirringstirred at rt for 20 min
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe celite pad was washed three times with acetone
  4. customThe combined filtrates were evaporated
  5. customThe phases were separated
  6. dry with materialphases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-e09fc660ab5041468a30252afde9812a
出典データセット
uspto-grants-2014_01
特許番号
US08637508B2

反応ノート

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