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Water → 2-(7-Hydroxymethyl-benzo[b]thiophen-3-yl)-ethanol

HRID 221932
ノート
印刷プレビュー

反応式

HRID 221932 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][C:13]1[C:14]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22](OC)=[O:23])[C:15]=2[S:16][CH:17]=1)=O)C.C(OCC)(=O)C.O>C1COCC1>[OH:23][CH2:22][C:18]1[C:15]2[S:16][CH:17]=[C:13]([CH2:12][CH2:10][OH:9])[C:14]=2[CH:21]=[CH:20][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2 回HCID 59488809Methyl 3-ethoxycarbonylmethyl-benzo[b]thiophene-7-carboxylate

生成物 1

HCID 594887992-(7-Hydroxymethyl-benzo[b]thiophen-3-yl)-ethanol収率 98%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

Under a nitrogen stream, to a solution (38 mL) of lithium aluminum hydride (0.74 g, 19.5 mmol) in THF was added a solution (30 mL) of methyl 3-ethoxycarbonylmethyl-benzo[b]thiophene-7-carboxylate (2.7 g, 9.7 mmol) in THF at 0° C., and the resultant solution was stirred for 10 minutes at the same temperature. To the solution was further added lithium aluminum hydride (0.74 g, 19.5 mmol) at 0° C., and the resultant solution was stirred for 10 minutes at the same temperature. Ethyl acetate was added to the solution, and then water (5.2 mL) was added thereto at 0° C. The temperature of the resultant solution was raised to room temperature, and then the solution was stirred for 10 minutes. The reaction mixture was filtered through Celite. Solvent was then removed by distillation under reduced pressure. The resulting residue was treated by addition of ethyl acetate and n-hexane (1:2), to thereby obtain the titled compound (1.97 g, 98%).

後処理

  1. customat 0° C.
  2. customat 0° C
  3. filtrationThe reaction mixture was filtered through Celite
  4. customSolvent was then removed by distillation under reduced pressure
  5. additionThe resulting residue was treated by addition of ethyl acetate and n-hexane (1:2)

出典と根拠

ORDレコード
ord-f07c633e182849bfb4fc1bd4762ba121
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08207134B2

反応ノート

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