Acetyl chloride → HCID 22143532、化合物

HRID 985195ノート

反応式

HRID 985195 の反応式
[C:1](Cl)(=[O:3])[CH3:2].CCN(CC)CC.[OH:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19]([CH3:21])[S:18][C:17]=2[CH:22]=1>C1COCC1.CCOC(C)=O>[C:1]([O:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19]([CH3:21])[S:18][C:17]=2[CH:22]=1)(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 122034952-Methyl-1-benzothiophen-6-OL

生成物 1

HCID 22143532HCID 22143532、化合物収率 126.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Acetyl chloride (1.5 ml, 1.66 g, 21 mmole) and Et3N (3 ml, 2.18 g, 21.5 mmole) were added, sequentially, to a solution of 6-hydroxy-2-methylbenzo[b] thiophene 8a (2.51 g, 15 mmole) in THF (120 ml) at 0°. The reaction was left stirring for 14 hours, gradually warming to ambient temperature, then diluted with EtOAc (100 ml) and washed with H2O (100 ml) and brine (100 ml). The combined aqueous layers were extracted with EtOAc (100 ml). The combined organic extracts were subsequently dried over Na2SO4 and concentrated, in vacuo, to give 3.9 g of a yellow solid which was purified by silica gel chromatography. Elution with hexane: Et2O (90:10) and evaporation of the appropriate fractions gave 2.93 g (93%) of a white solid. 1H NMR (DMSO-d6) δ7.70 (1H, d, J=8.6 Hz), 7.66 (1H, d, J=2.2 Hz), 7.12 (1H, s), 7.07 (1H, dd, J=2.2, 8.6 Hz), 2.54 (3H, s), 2.27 (3H, s). Anal Calcd. for C11H10O2S: C, 64.05; H, 4.89; S, 15.55. Found: C, 63.84; H, 4.93; S, 15.57.

後処理

  1. customat 0°
  2. waitThe reaction was left
  3. washwashed with H2O (100 ml) and brine (100 ml)
  4. extractionThe combined aqueous layers were extracted with EtOAc (100 ml)
  5. dry with materialThe combined organic extracts were subsequently dried over Na2SO4
  6. concentrationconcentrated, in vacuo

出典と根拠

ORDレコード
ord-ac36cef9815f4d20a87ee91a614982f3
出典データセット
uspto-grants-2005_03
特許番号
US06869962B2

反応ノート

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