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1,3-Propanediol → 2-(4-(tert-Butyl)-2-(1,3-dioxan-2-yl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole

HRID 2069851
ノート
印刷プレビュー

反応式

HRID 2069851 の反応式
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH2:20](O)[CH2:21][CH2:22][OH:23]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)=[C:9]([CH:10]2[O:23][CH2:22][CH2:21][CH2:20][O:11]2)[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 104421,3-PropanediolHCID 580161935-(tert-Butyl)-2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzaldehyde

生成物 1

HCID 594738142-(4-(tert-Butyl)-2-(1,3-dioxan-2-yl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole収率 49.8%

試薬・触媒・溶媒 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)触媒HCID 241Benzene
溶媒

実験手順

8.10 g (31.2 mmol) of 5-tert-butyl-2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-benzaldehyde was weighed into a 500 mL round bottom flask fitted with a stir bar and Dean-Stark trap. Added 300 mL of benzene and stirred to obtain a clear yellow solution. Added 383 mg (1.52 mmol) of pyridinium p-toluenesulfonate. Added 11.3 mL (156 mmol) of 1,3-propanediol. Heated the solution to reflux for 17 h. Cooled to room temperature Washed the reaction mixture with 200 mL of 50% saturated aqueous NaHCO3, 200 mL of water, and 200 mL brine. Dried over MgSO4 and removed the solvent on rotavap. Purified by silica gel flash chromatography using isocratic elution with 10% EtOAc/CH2Cl2 to obtain 4.93 g of the title compound as a clear yellow resin. MS (ESI) 318 (M+H)+.

後処理

  1. customfitted with a stir bar
  2. customto obtain a clear yellow solution
  3. temperatureHeated the solution
  4. temperatureto reflux for 17 h
  5. washWashed the reaction mixture with 200 mL of 50% saturated aqueous NaHCO3, 200 mL of water, and 200 mL brine
  6. dry with materialDried over MgSO4
  7. customremoved the solvent on rotavap
  8. customPurified by silica gel flash chromatography
  9. washelution with 10% EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-57f43ba78a5b4ddd8f96622196637b3c
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299077B2

反応ノート

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