Ethyl Acetate → HCID 13941270, compound

HRID 1644618Notes

Reaction equation

HRID 1644618 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC>ClCCl>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 66827Phenylboronic AcidHCID 75076Methyl 3,5-DihydroxybenzoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 13941270HCID 13941270, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3,5-dihydroxybenzoate (20 g., 0.12 mole, 1 eq), phenylboronic acid (30 g., 0.25 mole, 2.1 eq.), Copper II acetate (45 g., 0.25 mmole, 2.1 eq.), TEA (90 mL, 0.65 mmole, 5.4 eq.) in dichloromethane (200 mL) and 4 Angstrom molecular sieves (35 g) were stirred at ambient temperature for 24 h under nitrogen gas. The reaction mixture was filtered through silica gel 60 to remove copper acetate to give 8.8 g (30% yield) of crude product. Flash chromatography gave product at 40% ethyl acetate in an ethyl acetate/hexane system. The product is an off-white solid (2.0 g, 7% yield). 1H NMR (400 MHz, chloroform-d3) δ ppm 9.64 (s, 1H), 7.43 (m, 2H), 7.28 (s, 1H), 7.31 (s, 1H), 7.11-7.06 (m, 3H), 6.81 (s, 1H), 3.79s (s, 3H); Calc'd for C14H12O4; m/z (M+H+)=245; found 245.

Workup

  1. filtrationThe reaction mixture was filtered through silica gel 60
  2. customto remove copper acetate
  3. customto give 8.8 g (30% yield) of crude product

Sources & evidence

ORD record
ord-e87f48a0f2e945b1adb061592f9adce8
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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