Acetic Acid → 7-({4-[(4-chlorophenyl)ethynyl]benzyl}amino)-2,2-dimethyl-1H-1,3-benzodioxin-4-one

HRID 733637Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13](/[CH:16]=[N:17]/[C:18]3[CH:19]=[CH:20][C:21]4[C:26](=[O:27])[O:25][C:24]([CH3:29])([CH3:28])[O:23][C:22]=4[CH:30]=3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]3[CH:19]=[CH:20][C:21]4[C:26](=[O:27])[O:25][C:24]([CH3:28])([CH3:29])[O:23][C:22]=4[CH:30]=3)=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 7-[((E)-{4-[(4-chlorophenyl)ethynyl]phenyl}methylidene)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (1.65 g, 3.97 mmol), sodium triacetoxyborohydride (2.52 g, 11.9 mmol) and acetic acid (0.34 mL, 5.95 mmol) in anhydrous DCE (100 mL) was heated at 50° C. for 3 h. Then the reaction mixture was diluted with H2O (100 mL) and a saturated aqueous solution of NaHCO3 (100 mL) and extracted with DCM (3×200 mL). The combined organic layers were dried over MgSO4 and the solvents were removed under reduced pressure. Precipitation by addition of pentane and filtration gave 1.30 g of the titled compound as a pale yellow powder (77%). M− (ESI): 415.9. HPLC, Rt: 5.05 min (Purity: 98.0%).

Workup

extractiona saturated aqueous solution of NaHCO3 (100 mL) and extracted with DCM (3×200 mL)
dry with materialThe combined organic layers were dried over MgSO4
customthe solvents were removed under reduced pressure
customPrecipitation
additionby addition of pentane and filtration

Sources & evidence

ORD record: ord-3ebabb37d35a4444bdf4a4f9cc260e53
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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