Acetic Acid → HCID 67263626、化合物

HRID 1041645

反応式

HRID 1041645 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 67263626HCID 67263626、化合物収率 84.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8995be8133c2489f9acb637fda7fc1be
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

関連ノート

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