Dichloromethane → 3-[4-(4-Acetyl-3-hydroxy-2-methyl-phenoxymethyl)-benzyl]-benzoic acid

HRID 1818508Notes

Reaction equation

HRID 1818508 reaction equation
[C:1]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16](O)[C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=[O:21])=[CH:12][CH:11]=2)=[C:6]([CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].C([SiH](CC)CC)C.B(F)(F)F.CCOCC.ClCCl>O>[C:1]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=[O:21])=[CH:14][CH:15]=2)=[C:6]([CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 666995643-{[4-(4-Acetyl-3-hydroxy-2-methyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acid

Product 1

HCID 666995743-[4-(4-Acetyl-3-hydroxy-2-methyl-phenoxymethyl)-benzyl]-benzoic acidYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-{[4-(4-acetyl-3-hydroxy-2-methyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acid (80 mg, 0.197 mmol), triethylsilane (250 μL, 1.57 mmol), boron trifluoride diethyl etherate (70 μL, 0.542 mmol), and dichloromethane (2 mL) is stirred 1 hr at room temperature. The mixture is diluted with water and extracted with ethyl acetate (2×10 mL). The combined extracts are dried over magnesium sulfate, filtered and concentrated. The residue is recrystallized from dichloromethane/hexanes to give (54 mg, 70%) the title compound, as a white solid. 1H NMR (DMSO-d6) δ 12.92 (bs, 1H), 12.85 (s, 1H), 7.78-7.82 (m, 3H), 7.27-7.49 (m, 6H), 6.72 (d, 1H), 5.23 (s, 2H), 4.06 (s, 2H), 2.52 (s, 3H), 2.04 (s, 3H). LCMS M−1 389.

Workup

  1. extractionextracted with ethyl acetate (2×10 mL)
  2. dry with materialThe combined extracts are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-9a5faf1e1032486dbf0b3eb3d5959d8e
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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