Triethylamine → HCID 49834557, compound

HRID 1627068Notes

Reaction equation

HRID 1627068 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:10]=2)O1.C(N(CC)CC)C.[C:28]1(=[O:33])[CH2:32][CH2:31][CH:30]=[CH:29]1>O1CCOCC1.O.[Cl-].[Na+].O>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([C@H:30]2[CH2:31][CH2:32][C:28](=[O:33])[CH2:29]2)=[CH:10][C:11]=1[C:16]([F:17])([F:18])[F:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135882-Cyclopenten-1-oneHCID 49834556HCID 49834556, compound

Product 1

HCID 49834557HCID 49834557, compound

Reagents, catalysts & solvents 2

HCID 218864351,4-Dioxane--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
25 °C

Procedure

[Rh(S-BINAP)(nbd)]BF4 (0.03 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-trifluoromethyl-phenol (preparation 9) (1.5 mmol) were added to a 25 mL-flask containing a magnetic stir bar and a septum inlet. The flask was flushed with argon. Triethylamine (1.5 mmol) and 2-cyclopenten-1-one (1.0 mmol) dissolved in 1,4-dioxane —H2O (6:1, 3 mL) were then added. The mixture was stirred for 6 h at 25° C. Brine was added, the mixture was extracted with ethyl acetate, and the solvents were removed in vacuo to afford the title compound. 1H NMR (300 MHz, DMSO) δ 10.37 (bs, 1H), 7.45-7.36 (m, 2H), 6.97 (d, 1H), 3.43-3.23 (m, 1H), 2.57-2.44 (m, 1H), 2.37-2.17 (m, 4H), 1.96-1.77 (m, 1H).

Workup

  1. additioncontaining a magnetic stir bar and a septum inlet
  2. customThe flask was flushed with argon
  3. additionwere then added
  4. extractionthe mixture was extracted with ethyl acetate
  5. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-16a95da123764c25af20e042525d3247
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

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