Nitroethane → HCID 72491400, compound

HRID 1010516Notes

Reaction equation

HRID 1010516 reaction equation
[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]

Participants

3

Reactant 2

HCID 6587NitroethaneHCID 6430550HCID 6430550, compound

Product 1

HCID 72491400HCID 72491400, compoundYield 90%

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b0d845fb269f4a21a285b71e4c26b4bb
Source dataset
uspto-grants-2011_07
Patent number
US07977315B2

Reaction notes

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