Acetic Anhydride → HCID 67552039, compound

HRID 480648Notes

Reaction equation

HRID 480648 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][C:3]=1[C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH2:23]([O:25][CH:26](OCC)OCC)[CH3:24].C(OC(=O)C)(=O)C>>[CH2:23]([O:25][CH:26]=[C:16]([C:15](=[O:22])[C:3]1[CH:4]=[C:5]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][C:2]=1[F:1])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:24]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 12971970HCID 12971970, compound

Product 1

HCID 67552039HCID 67552039, compound

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 3-(2-fluoro-5-(4-morpholinylmethyl)phenyl)-3-oxopropanoate (Preparation 3, 20.0 g), triethylorthoformate (21.5 ML) and acetic anhydride (21.4 mL) is heated at 150° C. in a round-bottom flask equipped with a Dean-Stark trap and condenser. After 4 h, the remaining acetic acid and triethylorthoforrnate are distilled off by heating the mixture to 100° C. at 0.2 Torr for 1 hr, leaving 22.9 g of the title compound as an amber oil. The crude product is used as is in the subsequent transformations. Physical characteristics: 1H NMR (300 MHz, DMSO-d6) δ 7.85, 7.60-7.45, 7.23, 4.36-4.17, 4.09-3.99, 3.56, 3.49, 2.34, 1.29-1.11, 1.08-0.99; MS (ESI+) m/z 366 (M+H)+.

Workup

  1. customequipped with a Dean-Stark trap and condenser
  2. distillationthe remaining acetic acid and triethylorthoforrnate are distilled off
  3. temperatureby heating the mixture to 100° C. at 0.2 Torr for 1 hr

Sources & evidence

ORD record
ord-0907639c5b92442ea85a0372a8424006
Source dataset
uspto-grants-2003_11
Patent number
US06653307B2

Reaction notes

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