Diethyl Ether → HCID 15698114、化合物

HRID 466421ノート

反応式

HRID 466421 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH:9]([CH2:15][CH:16]=C)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:20].[Na+].CCOCC>[Os](=O)(=O)(=O)=O.O>[C:10]([CH:9]([C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:18])[CH2:15][CH:16]=[O:20])([O:12][CH2:13][CH3:14])=[O:11]

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 15698113Ethyl 3-(4-methylphenyl)-3-oxo-2-(allyl)propanoateHCID 23667635Sodium periodate2 回

生成物 1

HCID 15698114HCID 15698114、化合物収率 87%

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒3 回HCID 962Water溶媒

実験手順

Ethyl 3-(4-methylphenyl)-3-oxo-2-(allyl)propanoate (74.21 g, 301 mmol, 1.0 eq), osmium tetroxide (100 mg, cat.), sodium metaperiodate (141.8 g, 663 mmol, 2.2 eq), ether (500 mL) and water (1 L) were mixed and stirred at room temperature. After 24 hours, an additional 110 mg of OsO4 was added and after another 24 hours, 200 mg more of OsO4 was added together with sodium metaperiodate (190 g, 888 mmol, 3.0 eq). After 4 days, the layers were separated and the ether layer washed with aqueous sodium bisulfite (1×500 mL) followed by brine (1×300 mL). The ether layer was dried (MgSO4) and the solvent removed in vacuo to yield 64.99 g of a dark brown oil. This oil was flash chromatographed over silica gel in 4:1 hexane/ethyl acetate to yield 37.5 g of an amber oil. NMR (200 MHz, CDCl3 ) δ 9.79 (s, 1H); 7.93 (d, 2H, J=9 Hz); 7.27 (d, 2H, J=9Hz); 4.87 (t, 1H, J=7 Hz); 4.13 (q, 2H, J=7 Hz); 3.37-3.08 (AB multiplet, 2H); 2.40 (s, 3H); 1.14 (t, 3H, J=7 Hz). Anal. Calcd. for C14H16O4 : C, 67.73; H, 6.50. Found: C, 67.53; H, 6.54.

後処理

  1. waitAfter 4 days
  2. customthe layers were separated
  3. washthe ether layer washed with aqueous sodium bisulfite (1×500 mL)
  4. dry with materialThe ether layer was dried (MgSO4)
  5. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-da07ee3e3f134be28f3351989bcef90c
出典データセット
uspto-grants-1992_10
特許番号
US05155118

反応ノート

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