Nitroethane → HCID 86677955, compound

HRID 246210Notes

Reaction equation

HRID 246210 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].[O:6]1[CH2:11][CH2:10][CH:9]([CH:12]=[O:13])[CH2:8][CH2:7]1.C1COCC1.CC(C)([O-])C.[K+]>CCOC(C)=O.O.C(O)(C)(C)C>[N+:1]([CH:4]([CH3:5])[CH:12]([CH:9]1[CH2:10][CH2:11][O:6][CH2:7][CH2:8]1)[OH:13])([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 6587NitroethaneHCID 8028TetrahydrofuranHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 86677955HCID 86677955, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 100 mL round-bottomed flask, nitroethane (1.42 ml, 26.3 mmol) and tetrahydro-2H-pyran-4-carbaldehyde (1.0 g, 8.76 mmol) were combined with THF (5 ml) and tert-butanol to give a colorless solution. Potassium tert-butoxide (197 mg, 1.75 mmol,) was added at room temperature. After 30 min at room temperature, the reaction mixture was diluted with EtOAc and water. The organic phase was separated, dried, and evaporated to provide 1.3 g (79%) of crude 2-nitro-1-(tetrahydro-pyran-4-yl)-propan-1-ol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ ppm 4.74 (quin, J=6.61 Hz, 1H), 4.61 (qd, J=6.80, 3.02 Hz, 1H), 3.91-4.10 (m, 7H), 3.60 (t, J=5.48 Hz, 1H), 3.28-3.54 (m, 3H), 2.20-2.28 (m, 3H), 1.89-2.00 (m, 4H), 1.11-1.74 (m, 16H).

Workup

  1. customto give a colorless solution
  2. customThe organic phase was separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-e59367aef5c945ea8154a80d46835259
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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