Acetyl chloride → HCID 10297882, compound

HRID 1078499Notes

Reaction equation

HRID 1078499 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([C:29]([OH:31])=[O:30])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[CH2:17][OH:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:32](Cl)(=[O:34])[CH3:33]>N1C=CC=CC=1>[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([C:29]([OH:31])=[O:30])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[CH2:17][O:18][C:32](=[O:34])[CH3:33])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 9844563HCID 9844563, compound

Product 1

HCID 10297882HCID 10297882, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.42 g (5.87 mmol) of the alcohol obtained in Example 12 in 12 ml of pyridine are treated with 0.63 ml of acetyl chloride for 30 min. The reaction medium is poured into ice cold water, and extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate and evaporated to give, after recrystallization from the ethyl acetate/hexane mixture, 1.67 g (63%) of a product which melts at 251° C.

Workup

  1. additionThe reaction medium is poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto give
  7. customafter recrystallization from the ethyl acetate/hexane mixture, 1.67 g (63%) of a product which melts at 251° C.

Sources & evidence

ORD record
ord-af24f61408d44fbb9dfad33d94d845f6
Source dataset
uspto-grants-1996_08
Patent number
US05547983

Reaction notes

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