Acetic Anhydride → HCID 57723933, compound

HRID 1987669Notes

Reaction equation

HRID 1987669 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([O:10][CH2:11][CH:12]=[CH2:13])[CH:6]([OH:9])[CH:7]=[CH2:8])[CH3:2].[CH3:15][C:16](OC(C)=O)=[O:17]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCN(CC)CC.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([O:10][CH2:11][CH:12]=[CH2:13])[CH:6]([O:9][C:16](=[O:17])[CH3:15])[CH:7]=[CH2:8])[CH3:2]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 10465389HCID 10465389, compound

Product 1

HCID 57723933HCID 57723933, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 21882572Triethylamine methylene chlorideSolvent

Procedure

To a solution of 2-allyloxy-3-hydroxy-pent-4-enoic acid ethyl ester (100 mg, 0.5 mmol) and DMAP (30 mg, 0.25 mmol) in CH2Cl2-Et3N (9:1, 10 mL) was added Ac2O (76 mg, 0.75 mmol). The resulting solution was stirred at ambient temperature for 1H. The solution was diluted with CH2Cl2 (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. washwashed with H2O (20 mL×2)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography with 20% EtOAc-hexane

Sources & evidence

ORD record
ord-f7543777c19340118387ed688d30c3f4
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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