Sulfuric Acid → HCID 72491401、化合物

HRID 970279ノート

反応式

HRID 970279 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][CH:9]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH2:10][CH:11]([OH:17])[CH:12]([N+:14]([O-:16])=[O:15])[CH3:13].OS(O)(=O)=O>CCOCC.O>[C:1]([O:17][CH:11]([CH2:10][CH:9]([CH3:8])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:26])[CH3:27])[CH:12]([N+:14]([O-:16])=[O:15])[CH3:13])(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 72491400HCID 72491400、化合物

生成物 1

HCID 72491401HCID 72491401、化合物収率 39.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
-10 °C

実験手順

A flask containing 1.15 g of acetic anhydride was cooled to −10° C. with a salt-ice bath, and 3.1 g of 4 was added with magnetic stirring under an N2 atmosphere. After 10-15 min, 25 mL of concentrated H2SO4 was added. The reaction mixture was allowed to stir for an additional 10 min, after which it was diluted with 40 mL of ether and 10 mL of H2O. The mixture was extracted three times with 15 mL of saturated aqueous sodium bicarbonate and once with 10 mL of saturated aqueous NaCl. The ether layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation to yield 1.40 g of a mixture of stereoisomers of the nitro acetate 5. 1H NMR δ (ppm) 5.4 (br m, CHOCOCH3), 5.2 (t, CH3C(CH3)═CH and CH2C(CH3)═CH), 4.4 (m, CHNO2), 2.1 (s, CH3CO2), 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. stirringto stir for an additional 10 min
  2. extractionThe mixture was extracted three times with 15 mL of saturated aqueous sodium bicarbonate
  3. dry with materialThe ether layer was dried over anhydrous MgSO4
  4. customthe solvent was removed by rotary evaporation

出典と根拠

ORDレコード
ord-99503cd974b94fcda899d91a36e96a83
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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