Triethylamine → 3-(2,4-Dihydroxyphenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester

HRID 493050Notes

Reaction equation

HRID 493050 reaction equation
NC(C)C[C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]=[CH:8][CH:7]1[CH3:14])=O.C(N(CC)CC)C.[OH:23][C:24]1[CH:29]=[C:28]([OH:30])[CH:27]=[CH:26][C:25]=1[CH:31]=[CH:32][C:33]([OH:35])=[O:34].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.CN(C=O)C>[CH3:14][C:7]([O:34][C:33](=[O:35])[CH:32]=[CH:31][C:25]1[CH:26]=[CH:27][C:28]([OH:30])=[CH:29][C:24]=1[OH:23])([CH:6]=[CH2:4])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 33594933-(2,4-dihydroxyphenyl)prop-2-enoic AcidHCID 219471233-Amino-1-(2,6,6-trimethyl-cyclohex-3-enyl)-butan-1-one

Product 1

HCID 669332403-(2,4-Dihydroxyphenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-1-(2,6,6-trimethyl-cyclohex-3-enyl)-butan-1-one (2.38, 11.3 mmol, 10) and triethylamine (2.30 g, 22.6 mmol) in anhydrous THF (150 mL) stirred for 5 min at 22° C. is added 3-(2,4-dihydroxyphenyl)-acrylic acid (2.04 g, 11.3 mmol). To this heterogeneous solution is added BOP Reagent (5.00 g, 11.3 mmol; Aldrich #22,608-4) in DMF (10 mL), and the subsequent homogeneous reaction mixture is stirred for 1 h. The reaction mixture is partitioned between ether (200 mL) and water (400 mL); the organic layer is removed and washed with ether (200 mL). The combined organic layers are washed sequentially with saturated sodium bicarbonate solution (200 mL) and brine (200 mL). The organic layer is dried over anhydrous magnesium sulfate, vacuum filtered and concentrated to give 3-(2,4-dihydroxy-phenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester as an oil that is purified by flash chromatography to give 11 as a colorless solid.

Workup

  1. customThe reaction mixture is partitioned between ether (200 mL) and water (400 mL)
  2. customthe organic layer is removed
  3. washwashed with ether (200 mL)
  4. washThe combined organic layers are washed sequentially with saturated sodium bicarbonate solution (200 mL) and brine (200 mL)
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate, vacuum
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f53dfc84a96345c68c2d8af6ec3d5292
Source dataset
uspto-grants-2009_05
Patent number
US07534751B2

Reaction notes

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