Aluminium lithium hydride → (4-(Benzofuran-2-ylmethoxy)phenyl)methanol

HRID 2061381ノート

反応式

HRID 2061381 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:22]=[CH:21][C:15]([C:16](OCC)=[O:17])=[CH:14][CH:13]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:22]=[CH:21][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 59603176Ethyl 4-(benzofuran-2-ylmethoxy)benzoate

生成物 1

HCID 66601277(4-(Benzofuran-2-ylmethoxy)phenyl)methanol収率 67.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Compound 93 (400 mg, 1.29 mmol) was dissolved in THF (15 mL) and LiAlH4 (49 mg, 1.29 mmol) was added portionwise, with vigorous stirring. The suspension was stirred at room temperature for 1 h. THF was evaporated off in-vacuo. The crude residue was taken up in EtOAc and washed with water, brine and dried (MgSO4). EtOAc was evaporated off in-vacuo to obtain (4-(benzofuran-2-ylmethoxy)phenyl)methanol (220 mg, 67%) as a crude product. This was dissolved in toluene (10 mL). The solution was cooled to 0° C. PBr3 (98 μL, 1.04 mmol) was added dropwise over 15 min. The resulting mixture was stirred at room temperature for 1 h. It was then washed with saturated K2CO3 solution and extracted with EtOAc (3×30 mL). The EtOAc layer was washed with brine and dried (MgSO4). The solvent was evaporated off in-vacuo to obtain 2-((4-(bromomethyl)phenoxy)methyl)benzofuran as a colourless oil, (132 mg). This intermediate was used in the following reaction.

後処理

  1. customTHF was evaporated off in-vacuo
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. customEtOAc was evaporated off in-vacuo

出典と根拠

ORDレコード
ord-4117c38ae444458282bea774e4053c7b
出典データセット
uspto-grants-2012_10
特許番号
US08283340B2

反応ノート

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