Acetic Anhydride → HCID 54475024, compound

HRID 1109018Notes

Reaction equation

HRID 1109018 reaction equation
[OH:1][C:2]12[C:14](=[O:15])[C:10](=[CH:11][CH2:12][CH2:13]1)[CH:9]([OH:16])[C:8]#[C:7][CH:6]=[CH:5][C:4]#[C:3]2.CN(C1C=CC=CN=1)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1>[C:26]([O:16][CH:9]1[C:10]2[C:14](=[O:15])[C:2]([OH:1])([CH2:13][CH2:12][CH:11]=2)[C:3]#[C:4][CH:5]=[CH:6][C:7]#[C:8]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 541270511,8-Dihydroxybicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-13-one

Product 1

HCID 54475024HCID 54475024, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 1,8-dihydroxy-bicyclo[7.3.1]-trideca-4,9-diene-2,6-diyn-13-one (product of Example 4, 32 mg, 0.149 mmol) in 1 ml of pyridine was added dimethylaminopyridine and 1 eq of acetic anhydride (14 ul, 0.149 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes and then pyridine was stripped off on rotovap and on high vacuum. This residue was purified on a silica gel column using 10% and 20% ethyl acetate/hexane mixture as the solvent system. The title compound was obtained as light yellow foam in 85% yield (32.4 mg).

Workup

  1. customThis residue was purified on a silica gel column

Sources & evidence

ORD record
ord-77d98551bd4a4f97a081968e54c9eed4
Source dataset
uspto-grants-1994_06
Patent number
US05318989

Reaction notes

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