Hydrochloric Acid → 4-(4-tert-Butyldiphenylsilyloxymethyl-phenyl)butyraldehyde

HRID 891

反応式

HRID 891 の反応式
[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH:29]2OCC[O:30]2)=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])([O-])=O.[K+].[K+].N1C=CN=C1.C([Si](Cl)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>C1COCC1>[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH:29]=[O:30])=[CH:22][CH:21]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 313Hydrochloric Acid2 回HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 94078tert-ButyldiphenylchlorosilaneHCID 196941342-[3-(4-tert-Butyldiphenylsilyloxymethylphenyl)propyl]-[1,3]-dioxolane

生成物 1

HCID 196941314-(4-tert-Butyldiphenylsilyloxymethyl-phenyl)butyraldehyde収率 42.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5.5 g (11.9 mmol) of the dioxolane 171 in 40 mL of THF at room temperature was added 40 mL of 4.0N HCl and the resulting solution was allowed to stir for 1 h. The mixture was neutralized with solid K2CO3, extracted with ethyl acetate and concentrated. The crude mixture was dissolved into 25 mL of CH2Cl2 to which was added 600 mg (8.8 mmol) of imidazole and 1.9 mL (7.3 mmol) of tert-butylchlorodiphenyl silane. The resulting mixture was allowed to stir overnight at room temperature and was then poured into 0.5N HCl and extracted with ethyl acetate. The organics were dried over MgSO4, filtered and concentrated. Flash chromatography (elution with 8% ethyl acetate in hexane) gave 2.12 g of the aldehyde 172 as an oil. 1H NMR consistent with the product.

後処理

  1. extractionextracted with ethyl acetate
  2. concentrationconcentrated
  3. dissolutionThe crude mixture was dissolved into 25 mL of CH2Cl2 to which
  4. stirringto stir overnight at room temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washFlash chromatography (elution with 8% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-991308a13d764cc0817ac696051b408e
出典データセット
uspto-grants-1998_03
特許番号
US05723459

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