Acetic Anhydride → HCID 53875201, compound

HRID 2256269Notes

Reaction equation

HRID 2256269 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:14]([CH:15]([OH:24])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][C:9]2[O:10][CH2:11][O:12][C:8]=2[CH:7]=1.CCN(CC)CC.[C:32](OC(=O)C)(=[O:34])[CH3:33].CN(C1C=CC=CN=1)C>C(Cl)Cl.CCOC(C)=O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[C:14]([CH:15]([O:24][C:32](=[O:34])[CH3:33])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][C:9]2[O:10][CH2:11][O:12][C:8]=2[CH:7]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 54563882HCID 54563882, compound2×

Product 1

HCID 53875201HCID 53875201, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (±)-5-(1,3-dioxolanyl)-[6-(1-hydroxy-3-phenylpropyl)]-1,3-benzodioxole (Compound 12, 182 mg, 0.554 mmol), Et3N ) (0.23 mL, 1.66 mmol), acetic anhydride (78 μl, 0.832 mmol) and dimethylaminopyridine (DMAP, 33.8 mg, 0.277 mmol) in CH2Cl2 (1.0 mL) was stirred at 23° C. for 16 hours. The reaction was diluted with EtOAc and washed with 1N HCl saturated ag. Na HCO3, brine. The organic portion was dried (MgSo4), filtered and concentrated in vacuo. Flash column chromatography (silica gel, 6:1 hex(EtOAc) gave 167 mg (82%) of the title compound.

Workup

  1. washwashed with 1N HCl saturated ag
  2. customThe organic portion was dried (MgSo4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2f56723559e4ec29ab25a0cb6c0a289
Source dataset
uspto-grants-1997_08
Patent number
US05654329

Reaction notes

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