Triethylamine → HCID 58764200, compound

HRID 859632Notes

Reaction equation

HRID 859632 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].C(N(CC)CC)C.[CH2:23]([C:25]1[CH:26]=[CH:27][C:28]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])=[C:29](O)[CH:30]=1)[CH3:24]>>[CH2:23]([C:25]1[CH:26]=[CH:27][C:28]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])=[C:29]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:30]=1)[CH3:24]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 58764173HCID 58764173, compound

Product 1

HCID 58764200HCID 58764200, compound

Procedure

Trifluoromethanesulfonic anhydride (0.47 mL, 2.8 mmol) followed by triethylamine (0.42 mL, 3 mmol) was added to a cooled 0° C. solution of 5-ethyl-2-(3-methoxy-propyl)-phenol (0.45 g, 2.3 mmol). The reaction was stirred for 1 hour and then warmed to room temperature. The reaction was partitioned between 1 N HCl and EtOAc. The organic extracts were washed with bring, dried over Na2SO4 and concentrated to a black oil. 1H NMR (400 MHz, CDCl3): δ 1.24 (t, J=7.6 Hz, 3 H), 1.89 (m, 2 H), 2.65 (d, J=7.6 Hz, 2 H), 2.75 (t, J=7.6 Hz, 2 H), 3.35 (s, 3 H), 3.40 (t, J=7.6 HZ, 2 H), 7.07 (s, 1 H), 7.14 (d, J=8.0 Hz, 1 H), 7.23 (d, J=8.0 Hz, 1 H).

Workup

  1. customThe reaction was partitioned between 1 N HCl and EtOAc
  2. washThe organic extracts were washed
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a black oil

Sources & evidence

ORD record
ord-693681aecd034d97b4691411ef593ba9
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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