Acetic Anhydride → HCID 10013476, compound

HRID 1987670Notes

Reaction equation

HRID 1987670 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([OH:12])[CH:10]=[CH:9][CH2:8][O:7]1)=[O:5])[CH3:2].[CH3:13][C:14](OC(C)=O)=[O:15]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCN(CC)CC>[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([O:12][C:14](=[O:15])[CH3:13])[CH:10]=[CH:9][CH2:8][O:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 12179940HCID 12179940, compound

Product 1

HCID 10013476HCID 10013476, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21882572Triethylamine methylene chlorideSolvent

Procedure

To a solution of trans-3-hydroxy-3,6-dihydro-2H-pyran-2-carboxylic acid ethyl ester (70 mg, 0.41 mmol) and DMAP (24 mg, 0.2 mmol) in CH2Cl2-Et3N (9:1, 5 mL) was added Ac2O (54 mg, 0.53 mmol). The resulting solution was stirred at ambient temperature for 2 H. The solution was diluted with CH2C12 (40 mL), washed with H2O (20 mL×2), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography with 20% EtOAc-hexane.

Workup

  1. additionThe solution was diluted with CH2C12 (40 mL)
  2. washwashed with H2O (20 mL×2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography with 20% EtOAc-hexane

Sources & evidence

ORD record
ord-fda76e20214e4d81b60427bd733314ac
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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