Ammonium Chloride → [6-(Benzothiazol-2-yloxy)-benzo[b]thiophen-2-yl]-methanol

HRID 1947483ノート

反応式

HRID 1947483 の反応式
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([O:14][C:15]3[S:16][C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[N:19]=3)[CH:12]=[CH:13][C:7]=2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C(Cl)Cl>[S:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[O:14][C:11]1[CH:12]=[CH:13][C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[S:9][C:8]=2[CH:10]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 68771517HCID 68771517、化合物

生成物 1

HCID 68768803[6-(Benzothiazol-2-yloxy)-benzo[b]thiophen-2-yl]-methanol収率 103.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) solution 6-(benzothiazol-2-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester (274 mg, 0.8 mmol) in DCM (8 mL) was added LAH (2 M in THF, 0.4 mL, 0.3 g, 0.8 mmol) and the reaction mixture was stirred (0° C., 3 h). The reaction mixture was treated with saturated aqueous NH4Cl (2 mL) and partitioned with DCM (20 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×15 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as a yellow solid (259 mg, 77%). MS (ESI): mass calcd. for C16H11O2S2, 313.0; m/z found, 314.0 [M+H]+.

後処理

  1. custompartitioned with DCM (20 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (2×15 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-489a61e9d2d74fee8be0f45c64486507
出典データセット
uspto-grants-2013_03
特許番号
US08399465B2

反応ノート

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