Acetyl chloride → HCID 20043437, compound

HRID 621372Notes

Reaction equation

HRID 621372 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([C:8]1[C:9](=[O:21])[CH2:10][CH:11]([CH:15]2[CH2:20][CH2:19][CH2:18][S:17][CH2:16]2)[CH2:12][C:13]=1[OH:14])(=[O:7])[CH3:6].C(N(CC)CC)C>ClCCl>[C:5]([C:8]1[C:9](=[O:21])[CH2:10][CH:11]([CH:15]2[CH2:20][CH2:19][CH2:18][S:17][CH2:16]2)[CH2:12][C:13]=1[O:14][C:1](=[O:3])[CH3:2])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 15614621HCID 15614621, compound

Product 1

HCID 20043437HCID 20043437, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.82 g (10.5 mmol) of acetyl chloride is added dropwise to a stirred solution of 2.54 g (10.0 mmol) of 2-acetyl-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-cyclohex-2-en-1-one and 1.06 g (10.5 mmol) of triethylamine in 50 ml of dichloromethane. The mixture is stirred overnight at room temperature, and then is poured into 100 ml of ice-cold water. The organic layer is separated and washed with 20 ml of dilute sodium bicarbonate solution, followed by 50 ml of saturated sodium chloride solution. The washed extract is then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The product can be purified by column chromatography employing tetrahydrofuran-hexane (1:2 by volume) as eluent to afford the title compound.

Workup

  1. customThe organic layer is separated
  2. washwashed with 20 ml of dilute sodium bicarbonate solution
  3. extractionThe washed extract
  4. dry with materialis then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product can be purified by column chromatography

Sources & evidence

ORD record
ord-a7428a4176f5446d87a819475955c97b
Source dataset
uspto-grants-1989_04
Patent number
US04824470

Reaction notes

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