Carbonothioic acid, O-(1-chloroethyl) S-ethyl ester → HCID 85885663, compound

HRID 389352Notes

Reaction equation

HRID 389352 reaction equation
[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[CH3:3].C([N+](CCCC)(CCCC)CCCC)CCC.[C:24](=[O:32])([S:29][CH2:30][CH3:31])[O:25][CH:26](Cl)[CH3:27]>O1CCCC1>[C:24](=[O:32])([S:29][CH2:30][CH3:31])[O:25][CH:26]([O:5][C:1](=[O:6])[CH:2]([CH3:4])[CH3:3])[CH3:27]

Participants

4

Reactant 2

HCID 13557094Carbonothioic acid, O-(1-chloroethyl) S-ethyl esterHCID 21900164HCID 21900164, compound

Product 1

HCID 85885663HCID 85885663, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetrabutylammonium isobutyrate (5) (382 mmol) in tetrahydrofuran (500 mL) was added compound (2) (49 g, 288 mmol). The mixture was stirred at ambient temperature for 16 h then the solvent removed in vacuo. The residue was dissolved in diethyl ether (600 mL), washed with water (3×300 mL) and the organic phase was separated, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by vacuum distillation (60° C./240 mTorr) to afford the product (7) as a colorless liquid (40 g, 63%). 1H NMR (CDCl3, 400 MHz): δ 1.2 (d, 6H), 1.35 (t, 3H), 1.5 (d, 3H), 1.55 (m, 1H), 2.85 (dq, 2H), 6.95 (q, 1H).

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in diethyl ether (600 mL)
  3. washwashed with water (3×300 mL)
  4. customthe organic phase was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. distillationThe residue was purified by vacuum distillation (60° C./240 mTorr)

Sources & evidence

ORD record
ord-acc15745391840cca3569b2dd8f990c4
Source dataset
uspto-grants-2013_02
Patent number
US08378137B2

Reaction notes

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