Acetyl chloride → HCID 22143532, 화합물

HRID 985195노트

반응식

HRID 985195 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 22143532HCID 22143532, 화합물수율 126.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ac36cef9815f4d20a87ee91a614982f3
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06869962B2

반응 노트

불러오는 중…