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

HRID 1947483노트

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HRID 1947483 반응식
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

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 68771517HCID 68771517, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-489a61e9d2d74fee8be0f45c64486507
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399465B2

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