Acetyl chloride → HCID 67791890, compound

HRID 1741970Notes

Reaction equation

HRID 1741970 reaction equation
[Si:1]([O:8][CH:9]1[CH:14]2[CH2:15][O:16][N:17]=[C:13]2[CH2:12][CH:11]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:10]1[OH:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35]>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)C>[C:34]([O:26][CH:10]1[CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH:14]2[CH2:15][O:16][N:17]=[C:13]2[CH2:12][CH:11]1[O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:21])(=[O:36])[CH3:35]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67793159HCID 67793159, compound

Product 1

HCID 67791890HCID 67791890, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

4,6-Bis(tert-butyldimethylsilyloxy)-5-hydroxy-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole (401 mg) was dissolved in 20 ml of methylene chloride. Five milliliters of triethylamine and 0.5 g of 4-dimethylaminopyridine were added, and 100 mg of acetyl chloride was then added, followed by stirring the mixture overnight at room temperature. The reaction mixture was diluted with diethyl ether, and washed with dilute hydrochloric acid, a sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution in sequence. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 355 mg of 5-acetoxy-4,6-bis(tert-butyldimethylsilyloxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole having the following property (yield 80%).

Workup

  1. washwashed with dilute hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2ce88319c6854ba8b3f3775f82f5d591
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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