Acetic Anhydride → HCID 54047966, compound

HRID 652012Notes

Reaction equation

HRID 652012 reaction equation
[Na].C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[CH3:14][Si:15]([CH3:46])([CH3:45])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37](O)[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:33][CH:32]=1>C(OCC)(=O)C>[CH3:46][Si:15]([CH3:14])([CH3:45])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]1[CH:32]=[CH:33][C:34]([CH:37]=[CH:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 5360545SodiumHCID 20198301HCID 20198301, compound

Product 1

HCID 54047966HCID 54047966, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The [4-(trialkylsilylalkylamino)phenyl]alkenoic acids may be prepared by condensation of the appropriate aldehydes or by dehydration of the corresponding substituted-phenyl-hydroxyalkanoic acids. For example, ethyl 5-[4-[14-(trimethylsilyl)tetradecylamino]phenyl]-2,4-pentadienoate is obtained by the Wittig reaction of 4-[14-(trimethylsilyl)tetradecylamino]benzaldehyde with the Wittig reagent, triethyl 4-phosphonocrotonate. Alternatively, these alkenoic acids are obtained by heating 4-[N-trialkylsilylalkyl-N-(methyl or acetyl)amino]benzaldehydes with the sodium salt of the carbanion of ethyl acetate or with a mixture of ethyl acetate, acetic anhydride and potassium acetate. The second method is illustrated by dehydration of ethyl 3-[4-[14-(trimethylsilyl)tetradecylamino]phenyl]-3-hydroxypropionate to yield ethyl 4-[14-(trimethylsilyl)tetradecylamino]cinnamate.

Sources & evidence

ORD record
ord-34d567c8f3024bbdbe483eca202b3325
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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