Hexane → HCID 86718316、化合物

HRID 1777081ノート

反応式

HRID 1777081 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.[Li]CCCC.[CH3:12][C:13]1[CH:22]=[C:21]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=[CH:20]2)[C:14]=1[CH:23]=[O:24].CCCCCC>O1CCCC1.O>[CH3:12][C:13]1[CH:22]=[C:21]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=[CH:20]2)[C:14]=1[CH:23]([C:4]1[S:5][CH:6]=[C:2]([CH3:1])[N:3]=1)[OH:24]

参加物

7

反応物 4

HCID 8058HexaneHCID 127484-MethylthiazoleHCID 15795689HCID 15795689、化合物HCID 178418339Butyllithium

生成物 1

HCID 86718316HCID 86718316、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

4-Methyl thiazole 4 (837 μL, 9.2 mmol) was added to 20 mL of tetrahydrofuran (THF). The mixture was cooled to −78° C. and stirred for 20 min. Afterward, 2.5 M nBuLi (2.45 mL, 6.1 mmol) was added slowly over the course of 15 min. The resultant mixture was stirred at −78° C. for 1 h, after which a freshly made solution of 2-methylazulene-1-carbaldehyde 3 (522 mg, 3.1 mmol) in THF was added slowly at −78° C. The reaction was stirred for 30 min and checked by TLC (50:50 Hexanes/EtOAc). Hexane was added at −78° C. and the reaction was warmed to room temperature. Water was added to quench the reaction and the organic layer was extracted into ethyl acetate. The extracts were washed with water and brine, dried with MgSO4 and purified using flash chromatography (ethyl acetate and hexane). The purified material was dried down into a purple solid. Yield: 768 mg, 93%. 1H NMR (400 MHz, CDCl3) δ 8.45 (d, J=9.85 Hz, 1H), 8.19 (d, J=9.54 Hz, 1H), 7.52 (t, J=9.82 Hz, 1H), 7.19-7.13 (m, 3H), 6.78 (s, 1H), 6.64 (s, 1H), 2.56 (s, 3H), 2.42 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 174.2, 152.2, 149.1, 140.6, 137.2, 136.1, 134.8, 132.4, 125.3, 123.8, 123.6, 118.7, 114.1, 67.8, 16.9, 15.6. HRMS (ES) 152.2, 149.1, 140.6, 137.2, 136.1, 134.8, 132.4, 125.3, 123.8, 123.6, 118.7, 114.1, 67.8, 16.9, 15.6. HRMS (ES) calcd. [M-H2O+H]+ (C16H14NS) 252.0925. found 252.0836.

後処理

  1. stirringThe reaction was stirred for 30 min
  2. temperaturethe reaction was warmed to room temperature
  3. customto quench
  4. customthe reaction
  5. extractionthe organic layer was extracted into ethyl acetate
  6. washThe extracts were washed with water and brine
  7. dry with materialdried with MgSO4
  8. custompurified
  9. customThe purified material was dried down into a purple solid

出典と根拠

ORDレコード
ord-efb8b21827b34bb5b6ed9c5cf1e1571e
出典データセット
uspto-grants-2016_02
特許番号
US09266847B2

反応ノート

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