Acetic Anhydride → HCID 53875201, compound

HRID 861688Notes

Reaction equation

HRID 861688 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-2f17e4b3f1b84e558c05cd90757cd088
Source dataset
uspto-grants-1998_02
Patent number
US05714621

Reaction notes

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