Triethylamine → HCID 59560293, compound

HRID 1177116Notes

Reaction equation

HRID 1177116 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([OH:16])[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[C:22]([F:24])[CH:23]=1.CCN(CC)CC>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][C:20]2[CH:19]=[C:18]([F:17])[CH:23]=[C:22]([F:24])[CH:21]=2)[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 25067323Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate

Product 1

HCID 59560293HCID 59560293, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran-6-carboxy-lic acid methyl ester (3e) (1 g, 0.0045 mol), 3,5-difluorophenylboronic acid (1.07 g, 0.0068 mol), Cu(OAc)2 (0.9 g, 0.005 mol), freshly activated 4A molecular sieves (4g) and Et3N (4 mL) in CH2Cl2 (25 mL) was stirred at room temperature under N2 for 48 hrs. The mixture was filtered through Celite and the filter cake was washed with CH2Cl2. The filtrate was concentrated to give a dark liquid. The crude liquid was purified by column chromatography eluting with EtOAc/petroleum ether (1/5) to give the title compound (0.4 g, 26.6%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.18 (s, 1 H), δ 7.14 (s, 1 H), 6.47 (m, 1 H), δ 6.36 (dd, 2 H), 3.81 (s, 3 H), 2.83 (s, 2 H), 1.41 (s, 6 H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customto give a dark liquid
  5. customThe crude liquid was purified by column chromatography
  6. washeluting with EtOAc/petroleum ether (1/5)

Sources & evidence

ORD record
ord-e22f7c9e675f4871b9d228af8b68758b
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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