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Acetyl chloride → methyl 2-(6-acetyl-5-methoxy-2,3-dihydro-1H-inden-1-yl)butanoate

HRID 900530
ノート
印刷プレビュー

反応式

HRID 900530 の反応式
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH:16]([CH:20]([CH2:25][CH3:26])[C:21]([O:23][CH3:24])=[O:22])[CH2:15][CH2:14]2>C(Cl)Cl>[C:5]([C:19]1[CH:18]=[C:17]2[C:13]([CH2:14][CH2:15][CH:16]2[CH:20]([CH2:25][CH3:26])[C:21]([O:23][CH3:24])=[O:22])=[CH:12][C:11]=1[O:10][CH3:9])(=[O:7])[CH3:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 23529443methyl 5-methoxy-2,3-dihydro-1H-indene-1-yl-butanoate

生成物 1

HCID 21942762methyl 2-(6-acetyl-5-methoxy-2,3-dihydro-1H-inden-1-yl)butanoate収率 68.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of AlCl3 (103 mg, 0.78 mmol) in methylene chloride (2.5 mL) at 0° C., was added acetyl chloride (0.044 mL, 0.63 mmol), followed by the addition of a solution of methyl 5-methoxy-2,3-dihydro-1H-indene-1-yl-butanoate (130 mg, 0.52 mmol) in methylene chloride (2.7 mL) dropwise. The mixture was stirred at 0° C. for 15 minutes. The ice bath was removed and the mixture stirred at rt for 16 hours. The mixture was poured over ice and 4 drops of conc. HCl were added. This mixture was extracted with methylene chloride twice. The combined organic layers were washed with water, 0.05 N NaOH and water. The organic layer was dried, concentrated, and purified by chromatography with 10% EtOAc:hexane to give desired product (103 mg, 68%). Rf=0.28 (4:1 hexane:EtOAc); GC-MS (+Cl): m/z=291 (M+); 1H NMR (DMSO-d6): δ 0.840 (m, 3H), 1.536 (m, 2H), 1.876 (m, 1H), 2.108 (m, 1H), 2.505 (s, 3H), 2.521 (m, 1H), 2.760-2.889 (m, 2H), 3.236 (m, 1H), 3.511 and 3.589 (s, 3H), 3.836 (s, 3H), 7.012 and 7.253 (s, 1H), 7.440 (s, 1H).

後処理

  1. customThe ice bath was removed
  2. stirringthe mixture stirred at rt for 16 hours
  3. additionThe mixture was poured over ice and 4 drops of conc. HCl
  4. additionwere added
  5. extractionThis mixture was extracted with methylene chloride twice
  6. washThe combined organic layers were washed with water, 0.05 N NaOH and water
  7. customThe organic layer was dried
  8. concentrationconcentrated
  9. custompurified by chromatography with 10% EtOAc

出典と根拠

ORDレコード
ord-69a19f33a2f24045a9cd4c0e65f2b4e8
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07358386B2

反応ノート

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