Nitroethane → HCID 46848349, compound

HRID 929409Notes

Reaction equation

HRID 929409 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[N+:27]([CH2:30][CH3:31])([O-:29])=[O:28].C1CCN2C(=NCCC2)CC1>>[N+:27]([CH:30]([C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:31])([O-:29])=[O:28]

Participants

5

Reactant 4

HCID 6587NitroethaneHCID 682631,1'-CarbonyldiimidazoleHCID 796956-Phenylhexanoic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 46848349HCID 46848349, compound

Procedure

6-Phenylhexanoic acid (0.154 g, 0.80 mmol) and CDI (0.261 g, 1.60 mmol) were added together and then reacted with nitroethane (0.090 g, 1.21 mmol) and DBU (0.306 g, 2.00 mmol) according to the general procedure. Purification by column chromatography gave 0.060 g (30%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.31 (m, 2H), 7.21 (m, 3H), 5.24 (q, J=7.2 Hz, 1H), 2.64 (t, J=7.6 Hz, 2H), 2.58 (td, J=3.2, 6.8 Hz, 2H), 1.69 (d, J=7.2 Hz, 3H), 1.68 (m, 4H), 1.37 (m, 2H) ppm; 13C NMR (100 MHz, CDCl3) δ 200.1, 142.6, 128.7, 128.6, 126.0, 89.1, 39.3, 35.9, 31.4, 28.7, 23.3, 15.2 ppm; IR νmax (cm−1) 3026, 2933, 2858, 1732, 1559, 1453, 1362, 1030, 749, 701; HRMS (FAB) calcd for C14H19NO3 (MNa+) 272.1257, found 272.1255.

Workup

  1. customPurification by column chromatography
  2. customgave 0.060 g (30%) as a yellow oil

Sources & evidence

ORD record
ord-a96c684f92f941ed8105d049829f668d
Source dataset
uspto-grants-2016_03
Patent number
US09295257B2

Reaction notes

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