3-Chloro-4-fluoro-1-benzothiophene-2-carbonyl chloride → (3-Chloro-4-fluoro-benzo[b]thiophen-2-yl)methanol

HRID 2097046ノート

反応式

HRID 2097046 の反応式
[Cl:1][C:2]1[C:3]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7](Cl)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[C:3]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[CH2:7][OH:8]

参加物

4

反応物 2

HCID 125946453-Chloro-4-fluoro-1-benzothiophene-2-carbonyl chlorideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 59277586(3-Chloro-4-fluoro-benzo[b]thiophen-2-yl)methanol収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice-cold suspension of 3-chloro-4-fluoro-benzo[b]thiophene-2-carbonyl chloride (5.46 g, 23.6 mmol) in THF (120 mL) was added lithium aluminum hydride (11.8 mL of a 1.0 M solution in THF, 11.8 mmol) dropwise. The mixture was stirred for 2 h then quenched with NaOH (0.35 N solution in H2O). The mixture was diluted with Et2O and the solution filtered. The filtrate was dried (Na2SO4) and concentrated. Purification by flash column chromatography (silica gel, hexanes/EtOAc, 8:2) gave the title compound (4.52 g, 96%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 7.57 (d, J=8.1 Hz, 1H), 7.31 (ddd, J=8.0, 8.0, 4.7 Hz, 1H), 7.06 (dd, J=11.3, 8.0 Hz, 1H), 4.97 (d, J=6.2 Hz, 2H),

後処理

  1. customthen quenched with NaOH (0.35 N solution in H2O)
  2. additionThe mixture was diluted with Et2O
  3. filtrationthe solution filtered
  4. dry with materialThe filtrate was dried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (silica gel, hexanes/EtOAc, 8:2)

出典と根拠

ORDレコード
ord-722b2b2194e34cb480deca79916359a7
出典データセット
uspto-grants-2013_05
特許番号
US08450307B2

反応ノート

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