Hydrochloric Acid → Acetic acid 2-cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester

HRID 1954266ノート

反応式

HRID 1954266 の反応式
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[C:24]4[C:23]([CH3:25])=[C:22]([CH3:26])[S:21][C:20]=4[CH:19]=[C:18]4[C:13]=3[CH:14]=[CH:15][CH:16]=[CH:17]4)[CH:9]=[CH:8][C:7]=2[OH:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:28](OC(=O)C)(=[O:30])[CH3:29].Cl>N1C=CC=CC=1>[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[C:24]4[C:23]([CH3:25])=[C:22]([CH3:26])[S:21][C:20]=4[CH:19]=[C:18]4[C:13]=3[CH:14]=[CH:15][CH:16]=[CH:17]4)[CH:9]=[CH:8][C:7]=2[O:27][C:28](=[O:30])[CH3:29])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 184307052-Cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol

生成物 1

HCID 53716940Acetic acid 2-cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester収率 99.7%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To 2-cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol (2.8 g, 7.5 mmol) in anhydrous pyridine (20 mL) at room temperature under nitrogen was added dropwise acetic anhydride (0.92 mL, 9.8 mmol). The reaction mixture was placed in the refrigerator. After 41 h the reaction was diluted and acidified with 10% aqueous hydrochloric acid to a pH of 1. The mixture was extracted with diethyl ether (500 mL), and the diethyl ether layer was washed with 5% aqueous hydrochloric acid (100 mL), twice with water (100 mL), brine (100 mL), and then dried (MgSO4). Concentration under reduced pressure gave the title compound as a white solid (3.1 g, 98%): (DMSO-d6) δ 8.48 (s, 1 H), 7.97 (d, 1 H), 7.47-7.43 (m, 1 H), 7.38-7.36 (m, 2 H), 7.28 (s, 1 H), 7.19 (d, 2 H), 3.14 (quintet, 1 H), 2.40 (s, 3 H), 2.37 (s, 3 H), 1.99-1.91 (m, 2 H), 1.69-1.40 (m, 6 H), 1.56 (s, 3 H). MS(EI), [M+] 414. Anal. Calc. for C27H26O2S: C, 78.23, H, 6.32, N, 0.00. Found: C, 77.68, H, 6.39, N, 0.04.

後処理

  1. additionAfter 41 h the reaction was diluted
  2. extractionThe mixture was extracted with diethyl ether (500 mL)
  3. washthe diethyl ether layer was washed with 5% aqueous hydrochloric acid (100 mL), twice with water (100 mL), brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration under reduced pressure

出典と根拠

ORDレコード
ord-5db30964823f4086a673e54d2ca4ea9d
出典データセット
uspto-grants-2000_09
特許番号
US06121271

反応ノート

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