Hydrochloric Acid → (5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-yl)methanol

HRID 1876430ノート

反応式

HRID 1876430 の反応式
[F:1][C:2]1[C:3]([F:16])=[C:4]([C:13](O)=[O:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.Cl.[OH-].[Na+]>>[F:1][C:2]1[C:3]([F:16])=[C:4]([CH2:13][OH:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 585663065,6-difluoro-2,2-dimethyl-3H-benzofuran-7-carboxylic acid

生成物 1

HCID 58566591(5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-yl)methanol収率 57%

実験手順

To 5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-carboxylic acid (735) (0.75 g, 3.29 mmol) was added 1.0 M of borane tetrahydrofuran complex solution (12 mL), and the mixture was stirred at room temperature overnight. The reaction was cooled to 0° C., acidified with 5 N HCl to pH 1, and then neutralized to pH 8 with 5 N NaOH. The mixture was extracted with EtOAc (80 mL×3) and the combined organic phase was washed with water (50 mL), dried over anhydrous sodium sulfate, and the solvent removed in vacuo. The product was purified by prep HPLC to yield (5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-yl)methanol (736) (0.4 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ 7.18 (t, J=9.0 Hz, 1H), 4.38 (s, 2H), 2.97 (s, 2H), 1.40 (s, 6H).

後処理

  1. temperatureThe reaction was cooled to 0° C.
  2. extractionThe mixture was extracted with EtOAc (80 mL×3)
  3. washthe combined organic phase was washed with water (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent removed in vacuo
  6. customThe product was purified by prep HPLC

出典と根拠

ORDレコード
ord-eca193d81df04c01b6f5d637c0d4bd96
出典データセット
uspto-grants-2012_11
特許番号
US08309600B2

反応ノート

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