Nitroethane → HCID 72491400、化合物

HRID 970278ノート

反応式

HRID 970278 の反応式
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6]/[C:7](/[CH3:16])=[CH:8]/[CH2:9][CH2:10]/[C:11](/[CH3:15])=[CH:12]/[CH:13]=[O:14])[CH3:3].[N+:17]([CH2:20][CH3:21])([O-:19])=[O:18]>>[CH3:15][CH:11]([CH2:10][CH2:9][CH:8]=[C:7]([CH3:16])[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH2:12][CH:13]([OH:14])[CH:20]([N+:17]([O-:19])=[O:18])[CH3:21]

参加物

3

反応物 2

HCID 6587NitroethaneHCID 6430550HCID 6430550、化合物

生成物 1

HCID 72491400HCID 72491400、化合物収率 90%

実験手順

To 2.93 g of 3 was added 5 mL of nitroethane with stirring. Approximately 5-6 g of Amberlyst A-21 was added, and the mixture was stirred at room temperature overnight. The mixture was filtered and the ion exchange resin was rinsed four times with 25 mL of dichloromethane. The filtrate was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation, which afforded 3.53 g (90%) of a mixture of stereoisomers of the desired nitro alcohol 4. 1H NMR δ (ppm) 5.2 (t, CH3C(CH3)═CH and CH2C(CH3)═CH), 4.4 (m, CHNO2), 2.2 (br s, CHOH), 2.0 (m, C═CHCH2CH2C(CH3)═CHCH2), 1.6-1.7 (all s, CH3C(CH3)═CHCH2CH2CCH3), 1.5 (d, CH3CHNO2), 1.2-1.5 (m, CH2CH(CH3)CH2), 0.9 (d, CH2CH(CH3)CH2).

後処理

  1. additionApproximately 5-6 g of Amberlyst A-21 was added
  2. stirringthe mixture was stirred at room temperature overnight
  3. filtrationThe mixture was filtered
  4. washthe ion exchange resin was rinsed four times with 25 mL of dichloromethane
  5. dry with materialThe filtrate was dried over anhydrous MgSO4
  6. customthe solvent was removed by rotary evaporation, which

出典と根拠

ORDレコード
ord-78b27481ada8466bb6967eb123b15e27
出典データセット
uspto-grants-2007_12
特許番号
US07312191B2

反応ノート

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