Tetrahydrofuran → tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-formylvalerate

HRID 1912104ノート

反応式

HRID 1912104 の反応式
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30](=[O:35])NCOC)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([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.O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(O)(=O)C>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([CH:30]=[O:35])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:15])([CH3:17])[CH3:16])([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

6

反応物 4

HCID 8028TetrahydrofuranHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 71114767tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate

生成物 1

HCID 86675057tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-formylvalerate収率 64%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
-78 °C

実験手順

tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate (4.61 g) and tetrahydrofuran (60 mL) were mixed. To the mixture was added dropwise diisobutylaluminum hydride (1.0 M in toluene) (13.1 mL) at −78° C. The mixture was stirred at −78° C. for 1.5 hr. To the mixture was added dropwise acetic acid (0.515 mL). After an addition of aqueous Rochelle salt at −20° C., the mixture was extracted with ethyl acetate. The organic layer washed with water, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/25) to give the title compound (2.60 g).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/25)

出典と根拠

ORDレコード
ord-d4fcddd7217f4f609f18389659ed9d23
出典データセット
uspto-grants-2013_12
特許番号
US08604069B2

反応ノート

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