Acetyl chloride → HCID 67247374, compound

HRID 2357049Notes

Reaction equation

HRID 2357049 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC=C)=[CH:9][C:8]=1[O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:2].[C:25](Cl)(=[O:27])[CH3:26]>C1(C)C=CC=CC=1.[Zn]>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][O:17][C:8]1[CH:9]=[C:10]([OH:13])[C:11]([C:25](=[O:27])[CH3:26])=[CH:12][C:7]=1[O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 67246790HCID 67246790, compound

Product 1

HCID 67247374HCID 67247374, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

The compound of example 65c (38 g; 112.5 mmol) was heated with acetyl chloride (9.74 ml; 137 mmol) and activated Zn (7.46 g) in toluene (250 ml) for 5 h (Synth. Commun. 1998, 28, 2203). to obtain the title compound which was processed as is routinely done and purified using flash chromatography (silica gel, 3% CH3CN in chloroform). Yield, 30 g (78.3%); MS (CI): 409 (M++29), 381(M+); analysis: C16H20O8 requires C, 56.47; H, 5.92; found: C, 56.05; H, 5.59%.

Sources & evidence

ORD record
ord-b59ea5c387bb4473bea5c74202f6df1b
Source dataset
uspto-grants-2010_07
Patent number
US07759387B2

Reaction notes

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