Acetic Acid → HCID 67263626, 화합물

HRID 1041645

반응식

HRID 1041645 반응식
[F:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.C(O)(=O)C.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:8]([NH:7][C:6]1[CH:11]=[C:2]([F:1])[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]=1[OH:9])[CH3:10]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 136277005-Fluoro-2-methyl-6-nitro-1,3-benzoxazole

생성물 1

HCID 67263626HCID 67263626, 화합물수율 84.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-Fluoro-2-methyl-6-nitro-benzoxazole (2.556 g, 13.03 mmol) was dissolved in Tetrahydrofuran (90 mL) and Acetic acid (4.5 mL, 79 mmol). Sodium borohydride (1.48 g, 39.1 mmol) was added and the reaction was stirred at room temperature for 90 min, then poured into 100 mL satd. sodium bicarbonate. The solution was extracted 3×50 mL DCM and the combined organics were washed with 1:1 brine:satd. sodium bicarbonate (50 mL) and dried over sodium sulfate, then conc. onto 10 g Celite. The crude product was chromatographed (120 g silica gel, ISCO, 0-20-40% EtOAc:Hex) to afford 2-Ethylamino-4-fluoro-5-nitro-phenol as a yellow solid (2.20 g, 84%). 1H-NMR (CDCl3): 7.55 (d, 1H, J=6.8 Hz), 6.26 (d, 1H, J=13.2 Hz), 5.51 (s, 1H), 5.05 (s, 1H), 3.26 (m, 2H), 1.34 (t, 3H, J=6.8 Hz).

후처리

  1. additionpoured into 100 mL
  2. extractionThe solution was extracted 3×50 mL DCM
  3. washthe combined organics were washed with 1:1 brine
  4. dry with materialsodium bicarbonate (50 mL) and dried over sodium sulfate
  5. customThe crude product was chromatographed (120 g silica gel, ISCO, 0-20-40% EtOAc:Hex)

출처 및 근거

ORD 기록
ord-8995be8133c2489f9acb637fda7fc1be
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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