Acetyl chloride → HCID 20203309, compound

HRID 978459Notes

Reaction equation

HRID 978459 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>C1COCC1>[C:18]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 126238624-(Thiophen-2-yl)butan-1-ol

Product 1

HCID 20203309HCID 20203309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude product from Step A was dissolved in 100 ml of THF and the mixture was cooled in an ice-water bath. Triethylamine (7.5 ml, 54 mmol) was added followed by dropwise addition of 3.8 ml of acetyl chloride (54 mmol). The mixture was allowed to stir overnight at ambient temperature. The solution was filtered and concentrated on a rotary evaporator. The residue was partitioned between ethyl acetate and dilute, cold 1N HCl. The organic phase was washed with saturated NaHCO3 solution, brine and then dried (Na2SO4). Evaporation of the solvent left 10.48 g of the desired acetate (98%) the solvent left 10.48 g of the desired acetate (98%) as a light yellow oil. 1H-NMR (CDCl3)δ7.2-6.6 (3H, m); 2.9 (2H, t); 2.45 (2H, t); 2.15 (3H, s); 2.0 (4H, m).

Workup

  1. temperaturethe mixture was cooled in an ice-water bath
  2. filtrationThe solution was filtered
  3. concentrationconcentrated on a rotary evaporator
  4. customThe residue was partitioned between ethyl acetate
  5. additiondilute
  6. washThe organic phase was washed with saturated NaHCO3 solution, brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent
  9. waitleft 10.48 g of the desired acetate (98%) the solvent
  10. waitleft 10.48 g of the desired acetate (98%) as a light yellow oil

Sources & evidence

ORD record
ord-0b649c7173f3445eb5c1a3a7dd108e5f
Source dataset
uspto-grants-1987_05
Patent number
US04665090

Reaction notes

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