Acetic Anhydride → HCID 58047685, compound

HRID 1888726Notes

Reaction equation

HRID 1888726 reaction equation
[N:1]([CH:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][C:9]=2[CH:10]=1)[CH3:5])=[N+]=[N-].C1C[O:23][CH2:22][CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(=O)C)(=O)C>C(OCC)(=O)C.O>[C:22]([NH:1][CH:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][C:9]=2[CH:10]=1)[CH3:5])(=[O:23])[CH3:21]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 58047600HCID 58047600, compound

Product 1

HCID 58047685HCID 58047685, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using ethyl 2-(1-azidoethyl)-1-benzofuran-5-carboxylate (4.34 g, 16.7 mmol) obtained in Reference Example 88, THF (17 mL), water (1.7 mL); triphenylphosphine (6.58 g, 25.1 mmol), ethyl acetate (5 mL) and acetic anhydride (2.4 mL, 25.1 mmol), an operation in the same manner as in Reference Example 37 was performed to give the title compound (2.42 g, yield 53%).

Sources & evidence

ORD record
ord-8f35f0f89be44e4894413ccb737eb725
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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