Benzoic Acid → HCID 21956516, compound

HRID 2241052Notes

Reaction equation

CN(OC)C(=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH3:12])[CH:5]=1.[C:16](O)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1([Mg]Br)C=CC=CC=1.CCOCC>C1COCC1>[CH3:12][C:6]1[CH:5]=[CH:4][C:9]([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:23])=[CH:8][C:7]=1[O:10][CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

N,3-dimethyl-N,4-bis(methyloxy)benzamide (Prepared from the corresponding benzoic acid following the standard literature procedure for the formation of Weinreb amide, 6.2 g, 29.6 mmol) was dissolved in anhydrous THF (110 mL) under nitrogen and the solution was cooled to 0° C. A solution of 3 M phenyl magnesium bromide in ether (15.0 mL, 44.4 mmol) was then added drop-wise while maintaining an internal temperature of 0° C. to 5° C. The resulting mixture was stirred for 3 h at 0° C. to 5° C. then quenched with 5% aqueous HCl (150 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuuo to give 9.2 g of the crude 39 that was used without additional purification. 1H NMR (400 MHz, CDCl3): δ 2.13 (s, 3H), 3.92 (s, 3H), 6.91 (d, J=8.8 Hz, 1H), 7.40-7.62 (m, 5H), 7.64-7.70 (m, 1H), 7.73-7.79 (m, 1H).

Workup

temperaturewhile maintaining an internal temperature of 0° C. to 5° C
customthen quenched with 5% aqueous HCl (150 mL)
extractionextracted with ethyl acetate (3×100 mL)
dry with materialThe combined organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuuo
customto give 9.2 g of the crude 39 that
customwas used without additional purification

Sources & evidence

ORD record: ord-9c90137b72c344939d4cca1517e4f3c2
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723393B2

Reaction notes

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