Triethylamine → HCID 66969799, compound

HRID 1510299Notes

Reaction equation

HRID 1510299 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][C@@H:13]([CH3:17])[CH2:14][O:15][CH3:16])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:16][O:15][CH2:14][C@H:13]([CH3:17])[O:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([O:1][C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2856454-Fluorophenylboronic acidHCID 59127146methyl 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

Product 1

HCID 66969799HCID 66969799, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of methyl 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]benzoate (3.53 g, 14.7 mmol), p-fluoro-phenyl-boronic acid (16.2 mmol), copper(II) acetate (2.94 g, 16.2 mmol), triethylamine (10.3 ml, 73.5 mmol) and freshly activated 4A molecular sieves (17.7 g) in dichloromethane was stirred at ambient temperature and under ambient atmosphere for 2 days. The reaction mixture was filtered, and the dichloromethane was removed in vacuo. The residual oil was partitioned between ethyl acetate and 2 mol/l hydrochloric acid. The ethyl acetate layer was separated, washed with aqueous sodium hydrogen carbonate and brine, dried over Na2SO4 and evaporated to give a residue, which was purified by column chromatograph on silica gel (20-60% ethyl acetate in iso-hexane, gradient) to give the desired ester.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe dichloromethane was removed in vacuo
  3. customThe residual oil was partitioned between ethyl acetate and 2 mol/l hydrochloric acid
  4. customThe ethyl acetate layer was separated
  5. washwashed with aqueous sodium hydrogen carbonate and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto give a residue, which
  9. customwas purified by column chromatograph on silica gel (20-60% ethyl acetate in iso-hexane, gradient)

Sources & evidence

ORD record
ord-9853352328fb4e0690e5f6ca34b7b9d5
Source dataset
uspto-grants-2012_07
Patent number
US08211925B2

Reaction notes

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