Ethyl Acetate → HCID 69422514, compound

HRID 459163Notes

Reaction equation

HRID 459163 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[C:12]1([CH3:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([OH:21])C.[C:22]([O-:25])([O-])=[O:23].[Na+].[Na+].[C:28]([O:31][CH2:32]C)(=O)C>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:21][C:15]1[C:16]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:17][C:12]([CH2:18][C@H:28]([O:31][CH3:32])[C:22]([OH:25])=[O:23])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 21863594Toluene ethanol

Product 1

HCID 69422514HCID 69422514, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

A solution of (2S)(4-Hydroxy-3-iodide-)-2-methoxy dihidrocinnamic acid (197 mg, 0.56 mmol), 4-methoxyphenyl boronic acid (170.7 mg, 1.12 mmol) and tetrakis(triphenylphosphine)-palladium (0) (8.7 mg, 0.5 mmol) in 11 mL of a mixture 20:1 toluene/ethanol together with 2 mL of a 2N Na2CO3 was heated to 120° for 16 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature and dilute with ethyl acetate (20 mL). It was washed with H2O (3×5 mL) and brine (3×5 mL). The combined organic layers were dried (MgSO4), filtered and concentrated under vacuum. The resultant crude was purified by column chromatography (silica gel, hexanes/ethyl acetate 8:2). Colorless oil (123 mg, 67%). 1H-NMR (200.15 MHz, CDCl3): δ 7.39 (dd, 2H, J=2.1, 6.4), 7.08–7.03 (m, 2H), 6.97 (dd, 2H, J=2.1, 6.7), 6.85 (dd, 1H, J=1.3, 7.5), 5.60 (s, 1H), 4.17 (q, 2H, J=7.0), 3.95 (dd, 1H, J=5.9, 6.4), 3.82 (s, 3H), 3.35 (s, 3H), 2.97 (d, 2H, J=6.4), 1.22 (t, 3H, J=7.2)

Workup

  1. washIt was washed with H2O (3×5 mL) and brine (3×5 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe resultant crude was purified by column chromatography (silica gel, hexanes/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-14d68095652a4c7188b8b8d9c32bb347
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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