Triethylamine → HCID 58406083, compound

HRID 68392Notes

Reaction equation

HRID 68392 reaction equation
[OH:1]/[N:2]=[CH:3]/[CH2:4][O:5][C@H:6]([CH2:8][CH:9]=[CH2:10])[CH3:7].C(N(CC)CC)C.Cl[O-].[Na+]>ClCCl>[CH3:7][C@@H:6]1[O:5][CH2:4][C:3]2=[N:2][O:1][CH2:10][C@@H:9]2[CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23665760Sodium HypochloriteHCID 90198734(E)-N-{2-[(2S)-pent-4-en-2-yloxy]ethylidene}hydroxylamine

Product 1

HCID 58406083HCID 58406083, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of C5 (8.6 g, 0.06 mol) and triethylamine (0.455 g, 4.50 mmol) in dichloromethane (150 mL) at room temperature was slowly added a 6% aqueous solution of sodium hypochlorite (90 mL) while maintaining the internal temperature between 20° C. and 25° C. After the addition, the organic phase was separated, dried and concentrated in vacuo Silica gel chromatography (petroleum ether/ethyl acetate=10:1) provided the product as a yellow oil. Yield: 5.70 g, 40.4 mmol, 67%. LCMS m/z 142.1 [M+H+], 1H NMR (400 MHz, CDCl3), δ 4.68 (d, J=13.2 Hz, 1H), 4.59 (dd, J=10, 8 Hz, 1H), 4.18 (d, J=13.2 Hz, 1H), 3.76 (dd, J=12, 8 Hz, 1H), 3.59-3.66 (m, 1H), 3.39-3.50 (m, 1H), 2.14-2.19 (m, 1H). 1.42-1.51 (m, 1H), 1.25 (d, J=6 Hz, 3H).

Workup

  1. temperaturewhile maintaining the internal temperature between 20° C. and 25° C
  2. additionAfter the addition
  3. customthe organic phase was separated
  4. customdried
  5. concentrationconcentrated in vacuo Silica gel chromatography (petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-09ee913218c8440ea6b025f74423a56a
Source dataset
uspto-grants-2014_09
Patent number
US08822456B2

Reaction notes

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